In my offer, I am contemplating asking that the current tenants be moved out prior to closing. 

Certainly they won’t do more damage than your sub-renter is willing/able to cover.Talk to your insurance agent about coverage for people renting from your renter and serving alcohol to minors who maybe crash on their way home, or a person says they were sexually assaulted at your sub rental. 

After years of contemplating, we are diving into real estate investing as a part of our long-term retirement strategy. 

If you don't have equity you really have something to contemplate...And driving a lower priced vehicle does not mean a rust bucket! 

@Lior Rozhansky, The strategy that @Michelle Costello is contemplating is to combine a primary residence sale and 1031 on the same property. 

As you contemplate early retirement, here are couple of ideas you may wish to explore.

I guess the reason I'm contemplating this decision is due to many people being successful in the field without college and I really want to get a head start.

Look into the history of sexual assault victims trying to get assaulted databases setup.

The ARV of the house is now at $250K and I'm contemplating another cash out refi, but would like the rent to be a bit more stronger before I do that. 

As a developer I typically value the land as a percentage of overall sales price and often will tie the land cost to the sales price in a subordination deal like you are contemplating.