How accurate is the data provided by AirDND in terms of price and occupancy or do you use a different website to analyze deals?

Those 4 tend to be the most popular sites for mid term rental listings.

He told me I was unable to hold 2 homes through a VA loan.

Tons of recreation as well so could be good for a short term rental or medium rental

However, he starts to talk about how you may sometimes overpay for a property because you are not necessarily worried about what the property is worth today but about the “long-term play.”

It's a means of producing income, not long-term wealth. 

My current hold up is I've yet to be able to systemize it.My problem is: I get roughly 75 probates a week inputted by my VA.

This will be a short amount of information in regards to me using the VA Home loan benefits.

Vanilla) 0% Down and 0% interest, 20 year term, Sellers's Asking Price- 8.314 Million-This would be ideal, the monthly Finance payment to Seller would be 23,094.44 and the Rents will cover that and leave another 10k in cashflow.

So now you worry about his ability to finish, so you want to make sure you write up something to hold his feet to the fire.