Once you figure out the payment schemes, next you have to see what kind of resources they have to help you. 80% of real estate agents fail or only make like 40k a year so you have to avoid those people and only focus on finding a niche.

I would have the current owner provide you proof of deposits for the last two years for the rent receipts (look for steady on time payments as well as consistent amounts.).

That currently is my plan, I have been trying to figure out though if I am planning on putting some money down, to keep the mortgage payment more reasonable, is using the VA loan still beneficial?

Can always make a large principal payment and recast the loan 

The money you spend on your Hawaii trip would be a down payment for a house.

I was blown away by the taxes - I really wasn’t prepared for how much they’d cut into my cash flow.

This just will not cut it in Orlando. 

This theft had to take a while and might have been done by someone who had training in the Electrical Trade.No Hop-head Dope Fiend is going to know to cut the PVC raceways and how to cut (multi-Family) power to avoid being an Extra Crispy Criminal.And just knowing what to take, and being prepared to remove it--correct tools, correct cutters, seems like specialized knowledge.This to me does not seem like theft of copper wire, but theft of specific components that will be used in the Trade on new construction.And the renters did not notice their power was cut, and come out and have a look, and Management and Maintenance did not see this happening?

My personal recommendation would be to network your butt off, find a smaller hotel investment company and either place your cash with them (if you have enough) and try and be as hands on of an owner as possible, or to go searching for deals and bring them to smaller hotel investment companies and have them cut you into the deal. 

If so, can additional funds be brought to the table to fund the new property's down payment?