I've heard of some hosts adding to the house rules that the guests must complete those steps after booking on the OTA platform, otherwise the booking will be canceled.At my company, we don't do background and credit checks for OTA bookings, but we do ask why they're renting a MTR and who will be staying with them.

If we rent our house out, the tenant would likely cover our entire mortgage, but our HOA costs are high (they were raised a lot recently).

Paying more only on one can give a chance to get the other house potentially refinance if the rates go down.

We are booking out now and should be full up for the most part by April.Our lake house isn't in as well traveled area as yours so it is hard to compare, but maybe ask AirBNB how their search impressions are calculated.

I understand the net profit amount would be higher if we continue to leverage and scale, but there is something to not having a mortgage on half or all of our portfolio that interests me from a psychological standpoint.

A STR can generate 3x or more than a LTR.Airdna can give you a rough estimate but you need to check similar houses on Vrbo and Airbnb to get the best idea of nightly rates and occupancy. 

So, should I continue to save and build up more capital to put down on a more expensive property, find something for less than 4-500, or pull some equity out of my primary and look for something with a higher entry price?

I bought a single family house last year using a VA loan and at the time I had 12 units.

For example in Texas a finder is limited to a maximum fee of 10% of the net amount received by the beneficiary, thereby eliminating from profitability a significant percentage of deals.This is the same over hyped, over promoted, over promised, under performing opportunity as note broker, house wholesaler, etc.

With the delayed settlement  agreement, would give you time to clean the house up a little and market the house using the short date sale method.