The garage and the fact that a long term tenant was in place paying market rent.

The only two ways to rectify this are (1) purchase the property far below market price or (2) significantly increase the property net income usually through some method of “repositioning”. 

I’m brainstorming ideas on how I can market myself to potential mentors in the STR game in order to gain experience.

Do this quickly because some counties have a time limit on when you can appeal.I recommend you research the market for:- Comparable Property Sales- Condition of your property, including anything that may affect your property's value- If you are really serious, an expert appraisal may be worth the effort.

If we can complete projects faster, we increase IRR and build trust.3) Market Risk- The longer it takes to complete a project, the more exposed you are to market fluctuations.This goes for all things Real Estate - BRRRRs, Flips, New Builds, Rehabs, etc.Real Estate is a wild ride I feel your pain, I've had this happen many times where the project is twice as long.

Renting to a friend can complicate things, especially if you're starting below market rent.

Educate yourself on the local market, network with other investors and agents, and always have a solid plan in place before making any investments.

I realizing the duplex conversion strategy is more complex I probably wouldn't try it on my first property, just want to get a sense of what's possible in the Chattanooga market :) Thanks!

Chicago, with its vibrant neighborhoods and strong rental market, is a prime location for this strategy.

It’s a market where cash flow is achievable without needing a massive upfront investment.