She refused any phone, text, or face-to-face communication, giving us no chance to negotiate.We called the police on-site several times to help us vacate the guest squatter, she insisted she was a tenant paying month to month, huge red gag.

It takes about 2 seconds.The face of the lock lights up and this has been very helpful when guest check-in after dark. 

But...there are many provisions that are *mandatory* and some clauses that are void or voidable on their face. 

This could just as easily blow up in your face, as you set the "new" price, get no applicants and have to drop the price later, perhaps back to where it was.

I will work to educate the tenant and make sure they don't do the same thing in the future, but I'm wondering what penalties I could face as a result.

You have identified the problems you face--figure out solutions for them (as best you can).Good Luck!

I do have a painter scheduled but again it barely gets over 50 in the winter months and he strongly advised me to wait. 

It is late in the current cycle and yes many people rushing in now could face problems.

I've always thought about breaking into the real estate field in terms of helping investers automate tasks, or create software that can solve general problems investors face when managing properties.However when I look, there aren't really any real estate companies that look to hire programmers or seem to have a need for them.

Thats kind of the idea of what I'm facing, I suppose I'd just really need to nail the due diligence part to ensure that it appraises appropriately.