I agree with most people in this forum that mid-term rentals are on the rise and gaining popularity. 

Thus, you kick any capital gains down the road. 5) The best part of the law says that once it has been an investment for a certain number of years, you can actually move into it, and once you have owned it for a certain number of years, the capital gains you kicked down the road can be rolled into the capital gains that is exempt as your personal residence.

Discuss this with the lender before proceeding.Partnership or Joint Venture:Structure the purchase with a partner or entity while maintaining the assumption in your name.This allows you to benefit from the entity's structure while complying with VA loan rules.Entity-Owned Financing:If assuming the VA loan isn’t feasible, explore refinancing into a non-VA loan owned by your entity after the property is acquired.4.

Rent out to roommates so I employ the "rent by the room" essentially.Pros:insane cash flowif your room offer is much better value than other places to live, tenants will stay awhilea small community can be built when your tenants become friends with eachothernever ending supply of tenants (at least in my area)Cons:CAN BE management intensiveWILL BE management intensive until you gain experience and know how to manageIf you employ this strategy, the BIGGEST risk/liability mitigator is being VERY clear from the start about your expectations and that you will evict if new tenant doesn't follow your rules.With my setup - I furnish the rooms and have all utilities covered. 

The idea is to re-fi in a single transaction, which, I assume, will have benefits over three separate transactions.

However, this structure provides two main benefits: 1) I don't have to build a big marketing machine to raise money.  

Look If you are thinking of house hacking, then who cares if the market is overrated or not, as of right now if you have been renting all of these years you have been loosing $25-40k each year by renting and not gaining from the Miami appreciation of the market.

I am just unsure if we can avoid capital gains taxes if we do the seller financing route. 

@Rachel Seymour-NewtonIf the smaller property is a strong deal with solid cash flow and tenant demand, it could make sense to buy now and start gaining experience.

Becoming familiar with how treasuries work also gives a lot of insight into how mortgage financing works because mortgage rates move with the 10-year treasury most of the time - so following the 10-year will give you insight into the real estate cycle as a side benefit.