@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Additionally, I would like to attempt to do the process Owner/Builder with subcontracting work out as well as doing some of the work I'm comfortable with (I have some experience with bathroom & kitchen remodeling an am not new to the construction industry).

Paulette,Thanks for sharing that awful experience. 

Continue Renting options (self-manage or PM) - Our initial experience has been smooth, but of course not perfect.

PMC staff are good at maintenance and maybe repairs, but they are NOT licensed contractors with years of real-world experience.

I plan on driving alot to find distressed or run down multifamily properties that possibly are owned by an out of state investor and reaching out however would like everyone's opinion or personal experience on some other creative ways.

A financial advisor with real estate experience can help you plan effectively.

Even if getting the permits winds up costing $30K, to me... it still seems worth it.Does anyone have any experience with something like this?

Hi @Dawn Bertrand, I'm sorry that you feel this way about your experience as a resident of JWB. 

Based on my 20+ years of real estate experience, I’d say renting the condo might not be the best option—$2,000/month rent minus $800 in condo fees leaves you with just $1,200 before taxes and maintenance, and seniors' condos can be tricky to rent.