This is purely anecdotal, but I've noticed that the top performing properties in my area lead with an exterior shot.

It's pure BS that you're going to pay $15k and someone's going to bring you a $50k profit.

There are still some good markets that will provide cashflow but you'll need to have realistic expectations when investing purely for cashflow. 

Congrats - house hack or pure rental?

Quote from @Anderson Banegas Cerrato: Elijah, this is pure fire, man!

So someone who is looking purely to maximize potential return (and has unlimited time) is unlikely to find this a good fit. 

I have financed a number of STR properties and they will usually be appraised as a pure real estate as vacant value and a cash flow adjusted commercial value, sometime separated as going concern and real property.  

If so, and you're looking at a purely rental property (not to live in at any point) you could consider opening a self-directed IRA to invest in the new property without having to pull money out and pay penalties?

The “moderate size” question is pure opinion.

In hindsight I can see all the mistakes I made but...pura vida.I do my proformas and try to calculate returns but I don't measure the value of investments purely on these terms like some others who've responded to you.