I have had realtors and family members say what I was doing was risky or impossible.

Yet, I struggle to accept that a short-term cash infusion creates such dramatic tax disadvantage, as opposed to immediate financing (which is often impossible or impractical to obtain.)

I am finding it is very hard/impossible to cash flow with house hacking, atleast in my area and the deals I am looking at. 

As for buy and hold, you’ll buy at a discount and the concern will be the quality/completeness of the remediation, which is almost impossible to verify..

-Finding it impossible to talk to the listing agent(s).

It's not impossible in my mind for your current situation.

I'm not going to say getting into RE is impossible at $20k a year, but you will increase your success rate exponentionally if you can move that needle up a bit more.

It's mathematically impossible. 

Something to keep in mind with STR, that's tied to why REI is a smart game to play - control is the name of the game.You want to control the guests and rates (vet them in hopes of avoiding property damage, set rates to attract those willing to pay more for quality)You want to control the costs (furnishings, consumables, cleaning/repair/plumbing/electrical)You want to control the property (choice of property, location, financing terms, well or city water, septic or city sewer, etc)This is all going to be very hard to do, if not impossible, if you don't OWN THE PROPERTY. 

You could claim the contract is void by virtue of impossibility as you cannot be trespassed off of your own property.