Like I said I'm super driven a former college athlete and I want to be the best.

Then, when attorneys get involved the situation destroys your entire world around you and now you are going down a very long road for recovery.

At this point in time, I would rather bet on a rental bounce locally (not necessarily in the city) based on a post-covid recovery, rather than perpetual shrinking cap rates in those hot out-of-state markets (given that cap rates here are potentially equal or better than those other markets atm, and we may be headed into a higher interest rate environment).That's not to say other markets won't make people money.

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provides support for the property tax appeals process.Additionally, it can help maximize renovations and improvements.A Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.

We are both former DI student-athletes competing in team sports (football & lacrosse).

Law provides for cost recovery and penalty here to preserve the safety and condition, but not extra improvements. 

If you are foolish enough to add to your cost by helping your tenant pay for the rest (added cash to pay down mortgage), then you would be just delaying the time to cost recovery, and minimizing the profit when you get there. 

I’ve followed your journey for a while now and as a fellow semi-professional athlete, I respect your hustle.  

That's 15 years before you start to make a profit.5 - If you include the potential loan in this, you should make profits from the cars, but without knowing what this might be (per year) per dollar of loan (and you will charged interest (unknown rate)) after the first $75k which will probably negate the added profits from the cars and delay your cost recovery even more.6 - My conclusion is this deal doesn't work very well at all. 

For many people, finding a new or better job will be a top resolution.The jobs market made quite a bit of recovery in 2021 after it took a major hit during the COVID-19 pandemic.