The median closed sales price in July 2020 was $329,000, as compared to $275,000 last July and $213,000 back in 2017, according to the Ulster County MLS.

•Compare your planned rent with recent lease signings, not just listed prices.

Unfortunately due to the property values, the cash proceeds will be disproportionately impacted by transactional costs associated with the financing (doc prep, appraisal, recording etc.) which will also hurt the available proceeds compared to the same LTV financing of higher value real estate that can better absorb these transactional costs. 

Quote from @Holly Barrett: So I'm comparing them w/Foremost on our Short Term Rentals, the quotes are $500-$1000 less than I am currently paying for each property per year.

This property is being acquired at $79K per unit, a sharp contrast to comparable apartments in the area selling for ~$140K per unit.

Just to make sure we’re both on the same page, I’m referring to the annualized total return that is included in the bigger pockets rental calculator — I wasn’t intending to compare RE to stocks, but maybe I’m missing something in your answer.  

There are HELOANS - at that juncture, your best bet is to evaluate what is called the blended rate and compare that to an entire new first lien (cash out).

But even if you want to do large deals, you need comparable reps.Technology has made it easy to "analyze" deals.

There are a lot of affordable properties in Knoxville, but the growth isn't terribly vibrant and the deman isn't what you'd expect for a city of that size and that close to the Smokies - you're mostly looking at college rentals for the meat of the move season, and the SF market, while it exists, doesn't really compare to Chattanooga. 

However, they will certainly require you to jump through more hoops compared to private and hard money lenders.