@Lucas LeBlanc I am not a fan of short term rentals, in part because I don't know enough about them.

If you have the option a mini-split can be used in a bigger space with ductwork already in place and a booster fan.

I'm not a huge fan of Dave Ramsey in the latter stages but you sound like the perfect candidate for his baby steps program. 

Is musemn Disctrict better or Fan district?

Keep in mind many times sewer lines will pass a regular home inspection IE home inspector flush's each toilet once.but once the homes are put into service that's when the **** hits the fan and your in for an expensive repair.. only sewer scope will assure you have a viable line once put into service.

You wouldn't want your oil change guy to schedule three appointments at the same time slot and then the guy that offers the most cash gets his oil change and the other 2 are SOL.   

I was planning to charge tenants between $75-150/month for both sides depending on the slot and size (there are a couple different sizes).

To compensate, tenants have fans and open the windows when they can.

I'm not a huge fan of borrowing from a 401 but also don't want to 'waste' a lifeline.  

I was just listening to this same episode today as I was installing ceiling fans and a stove in a couple of investors' properties.