Not to mention if you need to go FHA (assuming you plan to occupy a unit) you have to pass the self-sufficiency test. 

Since my tenants are usually homeowners it doesn't make sense for me, but even for the couple travel nurses I've had, the background/credit check was sufficient and seeing how they communicate with me prior to booking.

or, as you said, reach out to them on linkedin be sufficient place to start?  

Your primary insurance policy with $300,000 in liability coverage should be sufficient in 99.999% of all lawsuits.5.

Its quality over quantity. 

My current income is sufficient enough to cover my living expenses, live comfortably, and put a portion toward savings each month.

GFH is just like a lower version with fewer features that are not sufficient to automate a Short-term rental business.You can also consider using Ownerrez, I'm not trying to run an ad for them right now but Ownerrez is a great PMS, and it has seamless integrations with different rental channels.

Quality over quantity!

$20,000 is not going to be enough to buy an investment property and have sufficient cash reserves in almost any market UNLESS you house hack or are doing a flip or BRRRR. 

Buy quality, not quantity.