I’m fairly new to real estate investing but the house I live in is paid for and I have a rental property that is paying for itself and paying me too.  

2- how much capital gains do I have to pay in Puerto Rico after living in PR but selling a property located in FL. 

You said you live in Austin, no better way to learn than directly so, there is a syndication group Viking Capital LLC, that is buying/raising for a 252 unit property in NewBraunfels, about 45 min south of Austin, watch their webinar at their website below and they have an 82 pg slide show as well, then take a 3 hour trip to go see it, walk the property, go into office ask about the units available/leasing how the market is from the office staff, look around for quality of property/deferred maintenace needed then drive the area for other competitor properties.

I'd talk to the tenant and let them know that it will be harder to find a new place to live with an eviction on their record. 

Anyone on here very familiar with Ashland OR and or live or work there?

I live on the beach in FL and do all my biz, in Cleveland.

If this project manager fits that description than I would try to come to an agreement that you both can live with.

I also gave her the address of another problem house, next to the house I'm living in, that has a squatter living there and she's looking at doing a tax sale on that. 

I also live very frugally. 

I currently live near Frederick, Maryland.