My challenge is that its hard to find deals with a strong cash flow in MA due to high property prices and I am not seasoned enough (and brave enough) to start out with an out of state deal or an in-state property that would need major fixing.

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. 

@Justin Arcelaschi Keep analyzing deals everyday and eventually a 2-4 unit will come available in a market you’re willing to live in.

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. 

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

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

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

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.

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

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.