Brand new investor/ self-taught roadmap. Thoughts?

Question

Hey all, I'm currently roadmapping a self taught REI curriculum. I would like to pivot away from my current career and aggressively yet intelligently, replace my 9-5 with investing.

I have no experience or edge in this except for basic carpentry experience, good communication skills and a decent knack for rapid skill acquisition and retainment.
My desired strategy is buy and hold multifamily properties to build my portfolio.

Could yall review my list and tell me if there's anything I'm missing, as a budding self-taught RE investor? Or even just thoughts and opinions.
I'm coming from very limited resources (around 10k of liquid capital) and would especially appreciate some direction or materials for creative financing.
After the new year, I will have to time to regularly attend local REI meetups and network.

alternatively, if anybody is in the Denver, Houston or Minot area and willing to share some wisdom, let me know and I'll buy you a beer or a coffee.

1. Real estate math: vocab and underwriting spreadsheets

2. multifamily underwriting. Analyzing several different properties for practice

3. financing & valuation: learning debt,cap rates DSCR, LTV, debt yield, amoritization and refinancing

4. Physical property management: interviewing contractors and property managers on what actually breaks and seasonal maintenance costs.

5. deal acquisition: LOIs, negotiating, inspections, titles, environmental, leases, finances.

Thanks for all responses and criticisms.

Randy Schell · Answer

Replacing a 9 to 5 is a big dream and I admire the nerve it takes. One thing worth considering is keeping the paycheck until a rental or two has proven itself, since that steady income is what lets you learn without panic.

Randy, Bunklow

Marc Mora · Answer

Congrats @Justin Schiller! What are you looking to do in the end? I can connect you to resources and people. I was new once, I’d love to help brother!

Jarret Jarvis · Answer

Good list. The thing I'd add is how you're actually going to buy the first one with $10k, because that decides a lot. For most people starting where you are, that's house hacking: buy a 2–4 unit with an FHA loan, live in one unit and rent the others. You can put as little as 3.5% down, and the rents help cover your mortgage. It's one of the easiest ways to get into multifamily without much cash.

I'd also add:

• Talk to a lender now, before the new year, so you know what you can actually get approved for.
• Learn the landlord-tenant laws in whatever market you pick. They vary a lot between cities and states.
• Find a local agent who works with investors. They'll know which neighborhoods rent well and can send you deals to practice underwriting on.

Talk to a lender now, before the new year, so you know what you can actually get approved for.

Learn the landlord-tenant laws in whatever market you pick. They vary a lot between cities and states.

Find a local agent who works with investors. They'll know which neighborhoods rent well and can send you deals to practice underwriting on.

On creative financing like seller financing or subject-to: it's worth learning, but I wouldn't build your plan around it for the first deal. Get one conventional or FHA deal done, learn how it all works, then get creative.

Your carpentry skills are a real edge, by the way. Being able to handle small repairs yourself saves a lot of money early on.

Jon Marquez · Answer

Justin, I like that you’re putting together a roadmap before jumping into your first investment. One thing I’d really focus on is getting comfortable analyzing actual deals, including vacancy, maintenance, financing costs and reserves. With $10K available, understanding the upfront cash requirements is especially important.

I’m a Denver-area Realtor, and I’m curious: Would you consider living in your first property and house hacking, or are you focused strictly on investment properties?

AI-assisted draft, reviewed by me.

Arman Ahmed · Answer

You’re covering a lot of the right stuff already. With only $10K liquid, I’d spend a lot of time analyzing real deals, learning financing, and building relationships before trying to force a purchase. Your carpentry background can help too. And don’t feel like you have to buy in Denver or Houston. If you’re open to investing out of state, Midwest markets can be worth looking at because the lower entry prices may give you more options with limited capital.

Robin Simon · Answer

Congrats! One thing I would say is you really should narrow down the niche you are targeting especially property type, A lot of people have a lot of success focusing on one very specific segment (like small multifamily in Houston, TX) for example and I've seen many go wrong with "shiny object syndrome' trying to many different things even if it can be more exciting. From your post, I would say it seems like your net is still very wide, so I would suggest homing in a little more

Michael K Gallagher · Answer

not sure what your real goals are other than it sounds like getting out of your 9-5 but outside of having a large amount of capital to invest your best bet is likely a house hack to both add to your asset line and drop your expenses monthly. The only way to really "accelerate" things is to get into a scaleable income and stack the cash to make the moves you are looking to.

Drew Sygit · Answer

Focus on getting your first rental BEFORE creating grandiose plans.

John Leland · Answer

Congratulations "budding self-taught RE investor".

People on forums can give you ideas, but you have no way to vet either them or their comments. I’ve seen a lot of incorrect information here.

You are asking good questions that take some time to comprehend because there are quite a few "what ifs" along the way.

In my 30 years of investing, the one area I see that is most misunderstood by investors is acquisitions/purchasing. That is usually where people go wrong.

They simply buy the right property, the wrong way.

Some people are happy to have bought a property only to find out it's more work, expense and carries more unknowns than they expect. Join a REIA or get some training if you want the fastest way to success.

Stuart Udis · Answer

Absent a ton of liquidity acquiring sustainable real estate that will truly allow for you to replace W2 income is very challenging. Perhaps refocus your goals on using real estate to diversify and to shorten your W2 career. I believe for most that's a far more attainable and realistic objective.

Brand new investor/ self-taught roadmap. Thoughts?

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