I have experience in real estate wholesaling but would like to expand to doing flips, rentals etc. eventually to get into this full time. if no experience is an issue then how else are you supposed to get experience?

Eventually, you will need to leap into your 1st investment.

Still, not knowing where you are going is tough.For military folks, eventually they usually decide on a hub where they want to plant roots (usually when kids are closer to school age) and then the hub stays and the party in the military comes back to the hub.You have the VA benefits and they are great.

I'd like to invest back home in Ohio eventually (I lived in both Columbus and Dayton for about 5 years each), but I'm much more comfortable starting with something I can see regularly. 

But there are many communities nearby which will allow you and your boys to make memories, and eventually you can retire here.

If you rent it for a few years you will eventually lose that benefit.

But I had thoughts about buying in the pocono area to then eventually turn it into an STR, then buy a nicer more permanent Single family home that’s paid for by my rental properties.

If I haven't responded to you, I'll get to ya eventually.

There will eventually be a time where rent will cause me to cashflow.

There are plenty of cases of people getting away with it, sure, but the IRS will eventually find out if you keep doing it.