My initial goal is to have rentals that produce a combined $1500-$2000/month in cash flow after expenses.

It's more attractive to sell for the same reasons why it's more attractive to buy that way. 

I am in Florida and just to compare notes Florida property taxes versus New York taxes are night and day and can impeded on your ROI.Not to mention depending on the area Florida has a fantastic STR/AIRBNB cash flow attraction right now. 

Interest only mortgages look attractive, they can boost your cash flow way up for your rental.

Population density and low-income do not produce good results.Anway, I hope it works. 

If you had 100k in Canada and a job that produces 40k/yr, what would you do over the next 4 years in real-estate?

Otherwise, it could affect the type of clientele the home attracts and the amount of rent you can charge.

They urinate and poop all day, the feces attracts fruit flys, it's a mess even when cleaned several times a week.

On the other hand, not sitting and investing that money in perhaps a lower producing return but having the funds working all year may (perhaps) deliver a net higher return in the end.

But that is assuming a ski resort nearby and not just a nice touristy town that doesn't have a main commercial attraction for whom it makes sense to offer that subsidized housing.