Going the DSCR loan route is a great way to scale your portfolio. 

Just know you will be limited on your financing options going that route. 

I would keep it as a rental and when you have enough equity to do a HELOC I'd go that route.

I like that "what is easier to put a value on" I didn't think about it that way and given the amount of properties these folks probably do they'd probably take the most convenient route.

Many of the investors that I work with find that since they are not planning to manage the property investing out of state in a turn key investment strategy is the best route to good appreciation in a growing area and good cashflow.  

@Seth Rose I strongly recommend you find the best cash flowing property possible and buy it with financing out of the gates, rather than go the BRRR route. 1.

The only reason I've heard of Morris Illinois, is beacuse our family used to drive to central Illinois to camp and boat, and Morris is directly on Route 47.Are you currently investing in Chicago or near you in Joilet @Scott Meech?

LTR Backup Plan: I want to ensure that if the STR route doesn’t pan out, the property could sustain itself as a long-term rental (LTR).

Given your situation (demanding job, young family, special needs child), I would suggest doing the SFH route for your first investment, especially if it's OOS.

The first international route from Houston to our local airport opens in April of next year, so we're going to heavily target US buyers.