Adding in the rent from the other side, the property would still be pretty negative on cash flow (largely due to the FHA loan w/ minimum down, I know).MAYBE I could bring the rent up over the next 3 years to where there is positive cashflow; MAYBE appreciation will be such that I could sell at a gain in several years. 

Just as in anything there are always exceptions to the rule, but by in large there are not a ton of opportunities for investors targeting condos to make great returns.  

I've done a large number of deals in NC through my entity and have not been asked that.

Buy another and another until you have enough equity to refinance one for large amount of cash.

Also through syndication your getting tremendous economies of scale and protections compared to a SFH or duplex.

If you don't find a good deal you will need to put a large down payment to put it in a cash flow posistion.

I’m interested in having more than one door and I have been dancing around the idea of buying duplexes or quads, but I think boarding houses seem genius because it’s a single family so the loan would be easier to get and it not a large area to maintain.

Generally,Location+SF+Amenities+Market Demand = Rent (in dollars).Now think of the right side of that equation as a scale.

I've been looking at out-of-state investments and have been very interested in SFR within a 30 minute drive of large military bases, specifically in Fayetteville near Ft.

You will also learn to appreciate when a real estate agent is actually doing their job correctly, vs the large number of agents who just show up and do the bare minimum.What prompted me to take the course was that my first agent was not very good, but I couldn't actually truly assess and understand that without knowing myself, now I can confidently say that she wasn't very good, (lucky me, lol).Short Answer: There's not a glaring reason I can think of to not educate yourself on it, even if just for education's sake.I can't provide info on the 2nd part as I'm just not as familiar with specific MA to CT reciprocity and requirements.