If I'm investing out of market, I want to be sure the location isn't a pain to get to.

It's a real pain to enforce but it's worth it.The majority of carriers right now have a loss rule on new business that varies but goes something like this... they will not accept your new policy if you have a loss in the last 3 or 5 years.

I looked into a cash offer just to free myself but the offer was painfully low (putting me at a $60k loss).

That could be a big pain in California.

This couldn't be more of a true statement with the current clients I'm dealing with.. on one spectrum, I have clients that are incredibly respectful take my recommendations and listen and on the other I have people who are just plain rude and are a pain to work with. 

I am doing this completely remotely, which has been a massive pain/lesson learned (topic for another day).I signed a very high-level agreement (i.e. expectations simply say "drywall and paint") with him for drywall and paint work at my home for a total of $10KI have paid $5K as a down payment as well as ~$2K in materials over time, as neededThere have been multiple break-in's in the home, and he has done me favors of working with the police, and boarding things up.

@John Quiles Yes I've heard City of Decatur can be a pain.

Section 8 housing is a pain as a landlord/management company - we TRY to steer clear of it for this reason.

Should I show up every week and talk about where I think the pain is coming (multifamily, STR, etc)?

Much more than that if she was a professional squatter. 2500 is painful emotionally but it gets her out immediately and I can move on with my life.