We even (I still can't believe it) had a person stay in one of our units that is about $350 a night, who bought EVERY SINGLE PACKAGE (Romantic, Birthday, Breakfast, and Pizza/Smores Kit) and spent $1000 in packages alone.

Bundling both properties in a single study may reduce costs.

I have an outdoor pool that easily have 1k+ people using it every season and I never had single complaint due to the water quality.

That's about what I'll get in the stock market plus I'll be liquid (as opposed to underwater the first couple of years) and it's just push button. 

It could be either single family or multifamily.

Imagine if you had one single-family home.

I'm considering buying a small single family home near a hospital in the Midwest to turn into a MTR, and trying to decide if it's worth the investment to furnish vs. going straight to LTR.

I manage 350ish single family homes in Charlotte, NC.

They have a bigger single family home and a tiny home on the property, but there close proximity and shared driveway present functional problems that are undesirable for guests. 

He believes that area where he will be buying the new homes is going to appreciate and attract more MTRenters, but now, the big difference is that he would now have 3 properties that can go up (or potentially down) in value, go up (or down) in rent, and three times as many vacancies to fill.My back of the napkin assessment is that for only a drop in $200 a month in cash flow, he would control a lot more assets with growth potential and as rents rise over the coming years, the combined rents will increase to a total more than the single rent.HOWEVER.