Is this a person who is, from here, going to turn their life around from the desperate situation that they find themselves in right now, such that they are willing to take a Subject-To deal? 

From what I've seen in this area right now, it seems like you'd have a hard time paying market LTR rents and making a good spread. 

Don’t stress about perfection—choose what feels right and move forward.7.

I only have one right now, so the monthly subscription is a bit hefty for me.

Insurance is still an annual dog fight via my broker.Read your policy very carefully, consider replacement costs will probably be higher than estimatesResiliency is a requirement here.As far as sell or not....it'll depend on your determination to be here.This ain't the burbs of the bay area.Prepping for heavy rain right now.

In that case, I would have PMI until I refinanced, right?

It is all about having the right strategy. 

Keep in mind that office is down right now and it could take an extended period to fill.Try to determine why it hasn't sold for 2.5 years.

The second is a rehab property that I purchased for myself, I purchased it out right for 100k.

If the price was right on Turn-key maybe, but probably more of the fixer-upper that can be leveraged later on for additional property or sold for a nice profit.