After 1-2 years, rinse and repeat.

If you do this once a year for 10 years, you will be very rich when you are old. 

Ivan, I'm in Tampa too and I'm a lender with formal commercial credit background from two of the largest lenders in the world and 34 years of lending experience.

I'm about 2 years into this "helper role" or "apprentice" role if you will and I'm starting to take on larger and larger roles and run my own deals.  

So it looks like you would need around 4-5 years to get to break even by selling those stocks and paying the tax now. 

You have the ability to sell while limiting your capital gains tax because you lived in 2 of the last 5 years. 

I feel like a GC would have been able to get me better deals with contractors while taking away the headache of not having to babysit contractors through this 1.5 year ordeal.

You will regret it in 10 years when the house has 300k in equity.Right now, the house probably does NOT have 190k in equity.

I've been managing 70+ midterm rentals for over 3 years and we have never housed a traveling nurse - in our area, their stipends (or what they are willing to pay) are much lower than we can get in rents with other prospective guests/tenants.Utilities are included at all of our properties and that is common practice here. 

We spent 30k of our own money rehabbing, lived in the property for 3 years, did most of the work ourselves, and sold last summer for 195k.