I do intend to stay close to home - but home provides only annual opportunities and I’m looking for year round possibilities with tax deed properties. 

If rent is due on the 1st and late by the 5th, apply the late fee on the 6th and serve a 3-day notice immediately.

Since you're looking to expand into Florida and other states, I'd recommend starting by narrowing down your focus:Market Research – Florida has great opportunities, but each state and city has different laws, taxes, and demand drivers.

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

For now, it Looks like your roommate/tenant can cover half of your mortgage (plus hoa fees). 

“I’m literally the nation’s leading expert in tax liens and tax deeds,” he boasts in one installment.

I don't think he would allow someone that had to put the fee on a credit card.

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

Also never pay any upfront fees and go with a trusted lender who closes through a title company.