Following the advise of J$, I know that I want to sell it have one less thing to deal with so away it goes.
Just for anyone who is interested or someday does a google search and finds this forum thread, I will try to update is with what I learn and where I go wrong so that others can learn from my mistakes (and maybe some of you smart people out there can give my your two cents when I am headed down the wrong path).
If I was well up the tax bracket chain I wouldn’t have a lot of choice but to bite the bullet and pay the 15% capital gains tax and move forward. However, for me, that would be too easy.
From what I have learned in the 10% or 15% tax bracket, capital gains are taxed at 0% Federally, and 6% here in Georgia. However that is only for the amount that you have room left in those tax brackets. Example for 2016 the 15% tax bracket is up to $37,650, so if your income after deductions and all is $30,000 (your AGI), the first 7650 would be taxed at 0% and the rest at 15% (unless it was a huge gain and got into the 20% bracket, which I won’t unfortunately).
Here is where things get interesting, since deposits into tax deferred reduce your AGI, and I am going to clear enough in capital gains to fill the 15% bracket, every dollar that I put into a retirement savings account (401k, IRA etc) that is tax deferred makes room for a dollar of capital gains to pay 0%. This makes the marginal tax rate on earned income 15%(if earned income is less then the standard deductions, assuming question 1 is true), 25%(if its in the 10% bracket) or 30%(if its in the 15% bracket).
There are 2 things that I am still looking into,
If my earned income is below the 10300 standard deduction and personal exemption, will they off set capital gains?
How far can I push the limit before the Alternative Minimum Tax becomes an issue?
I am always up for any insight anyone has and I will post what I learn in case someone else goes through this later.