For those reasons, I'd start with the properties that have the higher interest rates to avoid losing the lower interest rates on the others.  

In fact the family and I are heading down towards Munster to start our feelers today as part of a road trip, heading further east until Valparaiso to look at all the local neighborhoods. 

I'm just getting started as a REI/flipper. 

Is this a good starting place or should I just wait for the auctions next year?

I am a small start up who is doing rehabs at this time.

Sometimes when a church is converted to residential the taxation may start at purchase or it could revert back to a date - that would be something to consider. 

Personally, I started in a market close to me as I wanted to do rentals so until I got my process down, I didn't want to venture too far from home.

We start showing rooms to prospective tenants right around a month before lease expiration.

I highly recommend you start with house hacking.

I see a lot of unnecessary risk in investing in another country.If you still want to do it, I would start off with something on the lower end that is still nice to see how it goes for a couple of years before making a major investment out of country.I would thoroughly research all expenses such as taxes insurance, permits etc.