Current debt against them is ~$2.8mm via individual recourse investment property mortgages.

No, you can not “buy an hoa”....you can only buy the individual properties...but, why do you think you’d want to?

Use the advanced function when you get to rental income and input each individual rent.

That being said individual Property stats that they post can be way off when they try to extrapolate the potential of STRs that are only offered for small portions of the year.

Also, do they tell you specifically for individual properties or just give an approximate answer?

I'm awaiting to hear this individuals assessment on my finances/ qualification.

(for those not in the know on the analytics, millions weekly is not millions of individual persons, it could be 100k people visiting 10,20,30+ times, and most often any connected person has gone thru re-targeting multiple times)There are some veterans out there who do well with less, although that's the point, veterans, they have developed skills and local market knowledge on how to do it in a niche manner. 

But with USAA being a big bank, the person I spoke with may have no experience with an individual investor.

There is individual hook ups for both - so I guess they can source their own (even though it might be a pain in the butt).

You'll have way to many questions when you begin, so I encourage you to write them all down and ask different individuals to get an answer.