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.

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

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. 

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.

I highly recommend you start with house hacking.

There's a ton happening in the city and folks are finally starting to catch on.Detroit was also the fastest appreciating market in the country the other month, so it's clear folks are catching on!

It's no guarantee but it's a good place to start.

Would I then start applying for DSCR loans?

My brother and I are starting to invest on the side ourselves, and from all the podcasts we've been listening to, we want to make sure we are doing things the right way to take advantage of any tax incentives.