I hear that can be difficult securing lending on two owner occupied properties in the same town / area.

We are still in the process of this as the city has been a little difficult to work with.

And by then, financing was more difficult so I couldn't qualify for a second home without selling the first.   

You are in a difficult situation.

This tenant has been whiny and difficult from the start and I feel like he is doing this to jeopardize showings. 

I'll be impacting the garage and yard, and would rather be in a position to not even deal with this as a negotiating point since the reality is whether I'm right or wrong, the tenant has the ability to make it more difficult if they're not happy. 

More difficult to see safe money-making opportunities, so it seems like, from my perspective, listings and contracts are being reported in small waves, as people dip their toes in. 

I wanted to see if there was anyone local to Purdue University that is involved buying or selling real estate.I am an electrician with backgrounds in mechanics and control systems(more information in my profile) and id be more than happy to share my skills in return for mentorship or just to network.Otherwise I was wondering if there are investors in this area (Tippacanoe and surrounding) that could shed some light on this area regarding how difficult it may be or areas to stay away from. 

retail is very difficult these days .

i think flipping is exceptionally difficult right now.