The city offers more affordability compared to the DMV area, with many renovated homes selling below 350k giving you a better chance at finding a property that fits your budget while avoiding sky-high prices.

Talk to a CPA to see how it fits your plan. 

Have these guys ever heard of Quicken or any of the online personal finance programs available to track spending?

Again, if the numbers work, and you can fit in the cost of a PM service, what's the holdup?

Showing ID is not only a safety measure for yourself and the other person, it also helps to reduce fraud if someone is unwilling to provide identification and is being this difficult with a simple ask, then I would also question whether or not they would be a good fit as a tenant

Anywhere that has consistent or slightly growing population and a decent job supply may be a good fit.

Hard money is a great financing program to get you going.

The S8 program was never designed to put S8 tenants in Class A rentals!

Similar for bathrooms if virtually all are multi bathroom but you find a single bathroom, making it multi bathroom via new construction could be a value add.There are more sophisticated value adds such as add multiple adus via bonus density program.  

If you do not have (2) full years of 1099 you can still get approved for a mortgage using a Non/QM program like a "1 Year 1099" program or Bank statements.