Talk to a local lender to know what you can afford.  2.Research how to do real estate transactions, get a good RE lawyer or find a good investment knowledgeable agent.

I will talk to my realtor tonight since he was there during the walkthrough.

Do you want to continue investing purely in STRs or are you interested in expanding your strategy?

Or should I break my promise to get into real estate in 2025 and continue to work part-time while going to college to afford a conventional 30-year mortgage on my first SF and use the "Building Wealth Through Single-Family Homes" plan? 

Despite my continual reminding him that beside his suggestion being ridiculous that he was a PASSIVE investor / limited partner, he continued some form of this behavior.  

It talks about all the material participation rules, and how to ruin a taxpayer's day.Having a W-2 job is likely a killer... but at the same time, if that W-2 is not material or if your reliance on that income is not material, then we say go for it.

(I am not talking about suits nor uniforms, but work pants that I use while doing rehabs.)

I can help you look into investments properties in the area or talk to clients potentially selling to find out of market deals, etc. 

Drive a 2009 car that is paid off.I'm taking this next year to rent in Chicago (rent is about 1600/month) but am starting to seriously think about house-hacking and want to start talking numbers now so that I might be ready to close about a year or so from now. 

You want to know how hard real estate syndications can make your money work for you, and how passive real estate investing stacks up to the returns you’re getting through other types of investment vehicles.In order to help answer that question, you should first know that we will be talking about projected returns.