I am new to the game with 1 property leased to section 8 under my belt and was about to buy another.

Look, we were for most part playing a game of American Football for a long time.

Howdy, I have been in the game for about 10 years now and have mid seven figures of real estate assets. 

I have debated about moving a house onto the property and either selling or renting the property or subdividing the property with multiple homes or even several tiny homes.

Even with HMLs, they would either want to see reserves, or you would still need to put in a little 'skin' into the game to make the deal workGood luck!

REALITY CHECK: THIS BUSINESS IS HARD.Wholesaling and buying houses off-market is a sales game—and sales is brutal.

You are ahead of the game. 

Use your W-2 income to qualify for multiple loans now, stack a few properties before quitting your job, and consider BRRRR or DSCR loans later to scale.

Also confirm if its a planned community sometimes they have multiple HOA (master and local) that this can fall under. 

If so, they can sell within 2 years and not pay capital gains taxes on the sell of the home.They could take that money and buy multiple rental homes in other areas if they wanted, or use the money to downsize in to a different home while still having money left over.