5 Mistakes Keeping New Real Estate Investors Stuck

Written by David Dodge  

Real estate investing looks deceptively simple from the outside. Buy a property below market value, rent it out or flip it, and watch the money roll in. Yet every single day I talk to new investors who have been “getting ready” for 6 months, 12 months, even 2 years… and still haven’t closed on their first deal.

They’re not lazy. They’re not stupid. They’re just stuck.

They’re stuck in an endless cycle of podcasts, YouTube videos, BiggerPockets forums, and spreadsheets that never turn into signed contracts. The excitement they felt when they first discovered real estate has slowly turned into frustration, self-doubt, and sometimes complete abandonment of the dream.

I’ve been there. I made every single one of the mistakes I’m about to share with you. And I watched hundreds of students repeat them until we fixed the root causes.

Today I’m going to show you the five biggest mistakes that keep 90% of beginner investors paralyzed—and exactly how to avoid them so you can finally take confident action and buy your first property.

Let’s dive in.

Mistake #1: Overanalyzing Every Deal (Analysis Paralysis)

This is the #1 killer of first deals.

You find a potential property on the MLS or through a wholesaler. You spend three hours running numbers in your fancy spreadsheet you downloaded from some guru. You tweak the ARV by 2%, play with interest rates, adjust rehab costs up and down, and suddenly it’s midnight. The numbers barely work. You decide it’s “not good enough” and move on.

Repeat this 47 times, and you’ve successfully wasted an entire quarter without ever making a single offer.

I call it “spreadsheet masturbation.” It feels productive, but nothing actually happens in the real world.

Here’s a real example from a student named Mark. Mark analyzed 127 properties in his first four months. He made exactly zero offers. His criteria were so strict that only a unicorn deal would pass. Meanwhile, three of the properties he passed on were bought by other beginners and are now cash-flowing $250–$400 per month each.

The Consequences

• You miss good (not perfect) deals
• You lose momentum and confidence
• You train your brain to look for reasons NOT to act
• How to Beat Analysis Paralysis

1. Create Simple, Written Deal Criteria

Write down exactly what you will buy. Example for a buy-and-hold investor

• Single-family or 2–4 units
• Built after 1950
• Minimum $200 positive cash flow at 75% of market rent
• Maximum 15 minutes from my target area
• Purchase price no higher than 80% of ARV minus rehab

If a deal checks these boxes, you make an offer. Period.

2. Use the “Good Enough” Rule

If the deal makes money under your worst-case assumptions (10% vacancy, 10% maintenance, 8% interest rate), it’s good enough. Perfect is the enemy of profitable.

3. Set an Analysis Time Limit

Give yourself 30–45 minutes per deal. Set a timer. When it dings, you either make an offer or move on.

4. Commit to a Weekly Action Goal

I make my students commit to analyzing 10 properties and making at least 5 offers per week—no matter what the circumstances. The numbers game works when you actually play.

Action step: Write your simple criteria on a notecard and tape it to your monitor today.

Mistake #2: Not Understanding Financing Options

Most beginners think, “I’ll just get a mortgage” and leave it at that.

Then they discover:

• Conventional loans require 20–25% down for investment properties
• They can’t get more than 4–10 financed properties
• Hard money sounds scary
• DSCR loans exist, but nobody explains them

So they freeze. Without clarity on how they will actually pay for the deal, everything else is theoretical.

I’ve seen people spend months looking at properties they literally cannot buy with the financing available to them.

Why Financing Clarity Is Everything

Your financing determines:

• How much down payment do you need
• How fast can you close
• How many properties can you own
• Your holding costs
• Your exit strategy

 How to Fix It—Fast

1. Schedule a Call With a Lender THIS Week

Not next month. This week. Find an investor-friendly mortgage broker or bank and ask them: “Here’s my situation—what are ALL my options for buying a rental property?” Write everything down.

2. Learn the Main Loan Types in One Weekend

Here’s the cheat sheet:

• Conventional: 15–25% down, best rates, limited to 10 properties
• FHA: 3.5% down, must live in the property 12 months (house hacking)
• DSCR (Debt Service Coverage Ratio): No personal income docs, based on property rent, 20–25% down
• Hard Money: 10–15% down + points, 12–18% interest, short term (great for flips or BRRRR)
• Private Money: From individuals, terms vary wildly
• Portfolio Loans: Local banks/cu’s that keep loans in-house, often 20–30% down

3. Build Your Financing Ladder

Decide the order you’ll use each type. Example:

Year 1: House hack with FHA → live for free

Year 2–3: BRRRR with hard money + refinance into DSCR

Year 4+: Scale with private money or commercial portfolio loans

When you know exactly how you’re going to fund deal #1, #2, and #3, the game changes completely.

Action step: Book a call with at least one investor-friendly lender before you read the next section.

 Mistake #3: Buying Without Proper Due Diligence

This one hurts—literally in the bank account.

I’ve watched new investors skip inspections to “save $400” and then discover $40,000 worth of foundation issues. Or they buy in a neighborhood they’ve never driven in at 10 p.m. on a Saturday.

Common due diligence skips:

• No professional inspection
• No sewer scope (hello, $25k root invasion)
• Guessing rehab costs instead of getting real quotes
• Trusting Zillow Zestimates for ARV
• Not pulling crime stats or sex offender maps
• Not verifying rental rates with actual landlords

 The Result?

You either lose your earnest money trying to back out, or you own an expensive lesson that bleeds cash every month.

How to Never Skip Due Diligence Again

1. Use a Proven Checklist: (I give my students a 57-point due diligence checklist—everything from flood maps to school ratings.)
2.  Always, Always, ALWAYS Get a Professional Inspection: And attend it yourself. I’ve found $15,000 issues myself that the inspector almost missed.
3. Get 3 Contractor Quotes on Every Rehab: Even if you think you know the costs. You don’t.
4. Drive the Neighborhood at Different Times: Friday night, Sunday morning, weekday afternoon. Talk to neighbors.
5. Verify Every Number Independently
6.  Rents: Call landlords advertising similar units
7. - ARV: Look at sold comps, not listings
8. - Taxes: Check the county website, not the listing

Due diligence is where you turn a good deal into a great deal—or walk away saving hundreds of thousands.

Action step: Download or create your due diligence checklist today. Never look at another deal without it.

Mistake #4: Trying to Go It Alone

“I’ll just figure it out on YouTube.”

Famous last words.

YouTube University is amazing for tactics. It is terrible for strategy and accountability.

I did this for my first year. I probably consumed 1,000 hours of free content. I closed zero deals. Then I paid a mentor $5,000 and closed three deals in the next four months.

The difference? Someone who had already made all the mistakes was telling me exactly what to do next—and holding me accountable when I tried to hide behind “research.”

Why Solo Investing Is So Slow

• You don’t know what you don’t know
• No one to bounce deals off
• No accountability = endless procrastination
• You repeat mistakes that others have already solved

The Fastest Way Forward

1. Find a Mentor or Coach
   • Someone who is where you want to be in 3–5 years. Yes, it costs money. It’s still cheaper than the mistakes you’ll avoid.
2.  Join a Local or Online Investor Community
   • Meetup groups, masterminds, Facebook groups where people actually DO deals.
3.  Get an Accountability Partner
   • Another beginner who is slightly ahead or at the same level. Text each other your weekly wins and offers made.

I still have three mentors I pay today—and I own over 100 units. The day you think you don’t need guidance is the day your growth stops.

Action step: Message one person this week who is actively investing and ask if they’d be open to a 15-minute coffee chat.

Mistake #5: Expecting Instant Results

This mistake sneaks up quietly.

You see the Instagram highlight reels—someone buys a duplex in month 2, house hacks, and quits their job by month 8. So you think that’s normal.

Then month 3 rolls around, and you haven’t closed anything. You feel like a failure. Motivation tanks. You quit.

Realistic first-deal timelines for most people:

• With a full-time job: 4–9 months
• With mentorship and aggressive action: 2–6 months
• House hacking: often fastest (60–120 days)

Why the Rush Kills Dreams

When you expect instant results, you take shortcuts:

• You skip due diligence
• You overpay
• You buy a bad deal just to “get started”
• You burn out and quit

How to Set Yourself Up for Long-Term Success

1.  Adopt a 12-Month Mindset
   • “I am committed to owning my first cash-flowing property within the next 12 months—no matter what.”
2.  Focus on Weekly Process Goals, Not Outcome Goals
   • Track these numbers every week:
   • Properties analyzed
   • Offers made
   • Conversations with lenders/agents/contractors
   • New things learned
3.  Celebrate Small Wins
   • Made your first offer? Celebrate. Got your first deal under contract (even if it fell apart)? Celebrate. These are proof that you’re moving forward.
4.   Remember: Skills Compound
   1. Every offer you make, every inspection you attend, every lender you talk to makes you 1% better. By deal #3, you’ll be light-years ahead of where you started.

The investors who win are the ones who refuse to quit after month 4 when the highlight reels say they should already be rich.

Action step: Write down your 12-month goal and three weekly process metrics you’ll track starting today.

Conclusion: Your Next Move

Let’s quickly recap the five mistakes that keep 90% of beginners stuck—and quietly drain years of their life:

1. Overanalyzing every deal instead of making offers (analysis paralysis)
2. Not understanding financing before you ever look at properties
3. Skipping due diligence and buying $30,000–$100,000 surprises
4. Trying to go it completely alone with YouTube as your only mentor
5. Expecting your first deal in 60–90 days and quitting when it doesn’t happen

Avoid these five traps and you will lap the field. Most new investors never do.

The difference between the people who own zero properties five years from now and the ones who own five, ten, or fifty is never intelligence, starting capital, or even the market they’re in.

It’s consistent, imperfect action… and having the right people in your corner so you don’t have to reinvent the wheel.

That’s exactly why I created Real Estate Skool.

Real Estate Skool is my completely free investor community where thousands of action-taking beginners and experienced investors help each other buy their next property faster.

When you join today (100% free), you get instant access to:

• Live weekly Deal Lab sessions where members pitch real deals and get instant feedback from the group
• The exact deal criteria templates, due diligence checklists, contractor scripts, and analyzer tools my private coaching students pay thousands for
• Private deal-sharing channels (members post off-market deals, wholesaler lists, and pocket listings daily)
• Direct access to me and my team in the Ask-A-Mentor channel (no paywall)
• Premium perks most paid communities charge $97–$297/mo for—like our BRRRR calculator, DSCR lender list, and pre-vetted contractor database

There is zero catch and zero upsell to join the core community. I fund it myself because I’m tired of watching good people stay stuck for years when a few small tweaks and the right circle would change everything.

It’s your move. Let’s build your future.