I took a gamble and lost haha.

Much like in the stock market trying to “time” the market is simply a gamble unless you have a crystal ball.

Anybody north of the border with some experience in this asset class?

There are no natural disasters. there are two major universities, there's a good amount of things to do, taxes are low (I see newer houses with lower taxes than some 100 year old midwest homes), the area is easy to get to, and the laws here are pretty friendly to investment as the government has taken the gamble of giving major tax breaks to corporations and this in turn has helped fuel the job market.As for the rental stock, the seasonal snowbirds seem to have enough money to either do long STR's or own second homes here.

It is a gamble.  

It's available at any Barnes and Noble, Borders, and I am sure Amazon.

Any locals here who can provide some insight on the area around Cumberland, IN on the border of Indy?  

Good areas border fringe areas which border terrible areas, etc. 

she had a gambling habit. 

BUT since i believe that today is the 1st day of the rest of my life it is not...hardest things was finding people to trust there are a lot of sharks  out there in them there waters... and since  I live in Canada getting the whole cross border things sorted.Early errors cost big  but the mistakes  helped me get to where  I am today  even thought they had a huge price tag (40 000  Canadian ) I consider it a small cost to learn what i needed to know to invest for the next 40 years.