In other words, how would I calculate the return (from a purely financial standpoint) of "investing" in a primary residence vs renting and putting the money elsewhere (perhaps even into an investment property, but also considering buying a business)? 

Private Money Lenders (Kiavi, LendingOne, Private Individuals) Fix and Flip productsWho did you get the loans through?

Putting 20% down really puts a dent on our liquid money but better (we think) than it just losing value in the bank. 

Roll it into the rent with a lease clause that anything over $X is split 50/50 between both tenants and you don't care who uses more water...In short, spend some money and make it a legal duplex or at least make it two separate units.

Definitely that was money making time in terms of operations and appreciation as well.Things have changed now, there is so many STRs now that people are renting for 100-150 USD a night which is like a motel price.Now it may make sense from the perspective of, if Poconos is where you travel a lot with family or you are buying full cash to park the money, or tax strategy or various other personal reasons could be there where it might make sense to invest there.But coming in from the perspective of an investor who are new or have little experience and are trying to build wealth from not too heavy asset portfolio.

Bryan, this is exactly how I got started.I used some cash savings but largely leaned on my HELOC.

Hi, I am a newbie trying to purchase an STR property and hoping to save on my taxes from my W2.Could someone please help me understand what type of loan is best for my situation?

I have about $250k saved at the moment.

If your monthly budget for this type of thing is $100, you're losing money. 

In this case, where they NEED to secure a new rental vs a case where they merely WANT to move, they’re expectations will become realistic VERY quickly.If a property owner could net the same amount of money doing a long term rental, then that’s what they’d do so to avoid the more work and less uncertainty of 30-90 day rentals.