How can I accomplish this given my circumstances?

You are only allowed to deduct expenses up to your rent amount in that circumstance.

But it is possible to avoid taxes on such profit under the right circumstances.

Fair is fair, but beyond that life circumstances can change from when a tenant was placed to the current day.

Something like Spring or Humble would probably work better.As far as timing of your first to second homes, usually your lender will require you to occupy the home for 12 months with a zero down VA loan unless you have a special circumstance. 

We encourage them to keep cashflowing properties if the circumstances work.A couple things to keep in mind.1.)

Buying a super expensive property with a military income can put you in a very dangerous situation if other circumstances that you can't control come into play.

There is no circumstance under which I would ever buy with seller financing and then rent to the former owner, least of all in New York, where it can takes months (years?)

I understand that FHA rules allow you to take a second FHA loan under certain circumstances, including moving over 100 miles away. 

“In California, tenants have the right to bring their service dogs and emotional support animals to live with them in many circumstances.