For my peace of mind, out of state investing is not for me.  

It could be a Happy Hour on a Friday afternoon in a casual environment like Katy Trail Ice House Outpost in Plano where they have lots of tables and space to get a drink, gather, meet and talk real estate.

I know it's a trend across the nation, but it seems like Portland has usually been more peaceful than these other cities.

Doesn’t mean you cant have a conversation (or better yet, get estimates up front and then talk to him about it next time) with him about it, a peaceful, normal conversation.

Assuming I owned free and clear but had the reserves to cover major damages I don’t think I’d really be concerned with the yearly fee and would pay it for peace of mind.  

In this environment, the fact that you even applied should be good enough for any lender.

The price jump is not surprising with the current real estate environment. 

I am leaning towards buying another rental, however lowering my primary mortgage increases cash flow as well and paying off your home is an accomplishment, that brings peace of mind.

As stated above, I came from a terrible environment (Camden, NJ) and the last thing I want is for my younger brother a little sister is to become a statistic.

Down payment (at least 3.5% if you go the FHA route), closing costs (2 to 3% of purchase price, all in), rehab costs (could easily reach 100k in today's environment if the property needs a lot of work)