Was it via docusign or some other online signing platform? 

And with brokerages now offering new agent programs where they will pay 100% of the expense to get licensed, there is literally no reason not to. 

And have you looked into the link below, the Invest Southwest program?

I offer an online payment portal to submit rent payments via ACH or CC - they "couldn't figure out how to use it" so I set us up to accept Zelle payments.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I've been doing my own bookkeeping on Quickbooks online and it doesn't take too long. 

FHA is for sure not going to be an option for him, last option is purchasing from an investor with owner financing, or lease to own program where he will not need traditional financing. 

If you decide to revisit STRs, you might want to explore properties where you can project expenses independently, such as using local STR forums or online tools to estimate maintenance, management, and occupancy costs.For networking and strategy-building, you might find local meetups or groups beneficial.

I picked her exactly because she had a good social and online footprint!!

There are many resources for you to connect online and in person.