I was eager to buy a home at the time, and while I’m not certain I’d sell at a loss, I’m also unsure of the best way to evaluate the financials.

Take the emotions out of it and evaluate on what the deal is telling you.Good luck!

If you’re familiar with the area or have tips for evaluating properties, working with brokers, or finding good contractors, I’d love to connect and learn from your experiences.Looking forward to being part of this community and sharing my journey!

I made the mistake of consolidating nearly all of my due diligence specifically to RTR, and was less diligent when it came to evaluating their partners. 

Unless you have a Roth, you can easily pay much more in taxes by investing in real estate through an SDIRA.

Makes for very easy updating.As for out-of-state, @Daniel Hyman is correct that any competent tax preparer should be able to handle different state returns using easily available resources. 

The biggest pro of using FHA and conventional financing is you can easily use them to house hack for 3-5% down payment which is an extremely low down payment. 

Last summer a contractor that was building us two pergolas and grilling stations had to take $3K off his bill because he passed the deadline he agreed was easily achievable.As for how to deal with your current situation, prodding is about all you've got.

In Indianapolis C to B class neighborhoods I have rarely seen insulation upgraded on rentals especially doubles that have never been owner-occupied.  4th air gaps,  poorly fitting windows, and doors can be easily corrected with proper caulk and weatherstripping (usually).

There’s no one-size-fits-all answer, but a quality advisor can help evaluate the best path forward based on your specific needs.