If yes, that's going to require a far different strategy than if you just want a few nicely located homes that will appreciate over the years to supplement your day job income and/or retirement.Be sure to include timeline too. 

My short term goal is to supplement part of my income so I can assist my fiancé with some of her grad school payments (she is about to start PA school in January).I think I am only looking for some experience to understand what to look for, but I would like to have a couple of toes in the water around the start of the new year.

I rent out the tiny house to supplement the mortgage on the main house in which I live with my family.

Essentially, we would like to supplement an income (my mother's) which is approximately $24,000 after taxes.

Really looking to supplement my current income with some passive income from SFH. 

That's another reason I am now supplementing my Bay Area rentals by investing out of state in a more landlord friendly area. 

I am normally aligned with your thoughts but we may be misaligned on this one.Offering packages may say 5 or more years for conservative purposes but many have plans to sell or refinance (supplemental loan) after the value add to realize the sponsor compensation on the sale, eliminate/reduce the preferred return, and to maximize IRR and increase the velocity of capital. 

The most modern units have resistive electric elements to supplement. 

Alternatively I could buy two cash flowing properties (say $50k each that cash flow $500/month) in a cheap area and use that income to supplement my rent.

Earn enough to leave W2 job, provide supplemental income while retired, having RE investment fund your retirements etc The ways to earn and learn seem endless.