And yes I tend to do that sometimes... start with just one question and then think of a second one while the fingers are doing the typing!

What's missing from much of this discussion is a real understanding of what the property is, ten acres in the heart of upstate New York Finger Lakes wine country, the desirability of that property as a vacation property on the one hand and the value of it as a vineyard on the other, and how local government (especially Yates County) is systematically trying to fight against the encroachment of moneyed OOS vacation-home buyers/STR operators  in the area.This is not some bland normal place where normal people live and operate.

Sadly, we're an industry of amateurs, so you've really got to be careful who you do business with so you don't waste time or money working with someone leading you nowhere.Ultimately, you'll want an agent who has their finger on the pulse of the market... have they conducted research on all available rental properties in the area?

Hope that helps, and fingers crossed your property weathers the storm without a hitch!

I love my day job and have every intention of continuing in that job until the FAA pries my medical out of my cold dead fingers, but thanks to my career field I have an incredible amount of schedule flexibility.

What’s your opinion on using a VA loan to secure a home 0% down that I’ll be at for 3-4 years, use the Air Force BAH to gain some equity to sell for appreciation, fingers crossed?

If this place is an older property, I don't know of many flippers who would take the $30k (hopefully, prayerfully, fingers crossed) deal if they could just get $10k now and buy the next one. 

And always start via self effort, you have the words database of knowledge at your finger tips.

To put it in @Michael Plaks metaphor, Why would you put a ring on their finger if your intent wasn't to marry them? 

I live in the finger lakes region, I have people telling me it's much more of a pain and hussle owning 4 units than duplexes.