From a purely financial standpoint, if (just IF) I wanted to be in the position to fund both private high school and an expensive out of state school for all three, I'd be looking at $1.44M all-in, staggered across 15 years, beginning in 4 years (using 60K/year math for both).  

Quote from @Ruiyue Guo: It is not discrimination if they are treating all applicants equally.It does sound like they are charging a lot of junk fees with no justification. $565 to process an application?

It's just if you're getting an STR to off-set taxes, it's kind of missing the forest for the trees. 

However, I still want to play devil's advocate and see whether there is any justification for this kind of investment with potential appreciation. 

That is where the $2K is coming from, so we do have justification to back up some of these estimates. 

If that's of importance we can talk about this further.A single member LLC is how most of us usually start.Creating a LLC doesn't make any difference on the Capital Gains tax...OTHER things affect this, but not JUST if the property is in a LLC or not.And the liability thing is always "touted" with LLC formations but very few people will do all of the OTHER things it takes to provide proper shielding. 

Forget for a moment the quitting thing, that was just listed as my justification for going large off the bat instead of starting small.I'm also not needing to count the rentals as income, I'm just wondering the implications of buying multiple properties (very high cap rates) vs one big one (low cap rate).

@Ben Petersen I’m fine making low offers but there should be a justification for it.

But there are a lot of double standards and self righteous justifications out there.

That would apply to someone who promises by means of a fully executed contract to buy the property and fails to do so without proper justification for backing out.