I have self employment income and no w2 employees.

If you have the cash and you want to buy a personal residence, it sounds like you have sufficient capital and income to support a new (modest) house and the losses you will incur on the condo. 

My question is should I sell now ( subject to short term capital gains, self employment taxes) or rent out and sell after the one year hold ( subject to long term capital gains) ?

Dear Bigger Pockets, I've been pretty thorough in my profile and it seems I have gone some distance toward  outing my inner nerd. Regardless, it's nice to "meet" you and great to be here. I'll be lurking in some forum...

After the housing crash, my long time tenants moved out and I was moving off to grad school, and I could not sell my house (I was way underwater on the mortgage), so I ended up renting it out.I only recently got above water on that house, and it is not the best investment property, but I'm keeping it for now since it is finally generating a positive cash flow.I've recently come into a lot more money (self-employed), and am now in a position to buy even more properties, but I want to do it right this time.

Once you find that out, call up the HOA management company or the HOA number if it's self-managed.

I'm im palm beach county my self and looking to do the same.

My account just put a damper on my plans to fund a Self Directed IRA this month with a 2015 max contribution, and a 2016 max contribution in early Jan, and to take those $13,000 to invest in a flip project I'm working on.

We self manage which helps on the costs and are able to keep our vacancy at almost 0.

All of which we self manage from all over the country.