You have to determine whether a refinance makes sense to you based on how much you can pull out, the reduction in the interest rate and the fees associates with it.Refinances(especially an FHA Loan) are not cheap and a $50,000 increase in value may potentially not justify a refinance.You may want to see if you can do a HELOC instead as it will likely be cheaper.You should take advantage of the Homestead benefits since you live in the property.

With lower money down and the ability to be hands on during the renovation made it more appealing to me How did you find this deal and how did you negotiate it?

Can you just raise his rent to an amount that compensates you for his lack of time keeping ability?

@Greg Scott I ran the numbers, to the best of my ability that showed that a HELOC was better than a mortgage. 

I have surpassed the ability to do a sec. 121 and avoid capital gains. 

Divide the cost of painting into the cost of the siding to determine how many times you can paint until it equals.exceeds cost of siding.EXAMPLE: $500 to paint versus $5000 to side.$5000 / $500 = 10 timesIf you have to repaint every 5 years then 5 x 10 times = 50 yearsIn this example if you only plan to own for 30 years, then it would cheaper to repaint every 5 years.This is a SIMPLE example.

The goal with the license is access to the MLS, the ability to make my own offers, and conduct BPOs which require a salesperson license. 

Your CPA might also recommend your llc being taxed as an S-Corp, but there are many variables that only you and your accountant will know and should know to determine the best tax strategy for you sir.

The purchase for your property is the reason I constantly state that investors need to look at hundreds or thousands of properties BEFORE MAKING A PURCHASE and the investors need to do the math for every property they look at a hundred times to determine what property will give them the best profit.

Because there is no income verification requirement for many of these loans, there is no real ability to repay other than rent.