Hi @Yvonne Acosta,I'm an agent working exclusively with investors in Fort Myers, and I can tell you that it's very difficult to find a condo here that cash flows well.

My major concern with not selling is missing out on the Home Sale Tax Exclusion - which would negate any taxes on capital gains up to $250,000 - as long as it's owner occupied 2 out of the last 5 years - which it has.Any advice on how I can capitalize on tax savings now and keep it as a rental? 

If "C" were to stop paying rent (while in the midst of the eviction process) there isn't another part of this lumped portion of your invested (and borrowed)funds generating income (with the exclusion from other investments obviously, just breaking this question and specific question apart)This leaves you in a bit of a quandary however as your renter quality at $700/mo and the other at $1200/mo could be different and you could also end up with a worse case situation than outlined (having dual evictions going vs one solid renter) -Giving the full argument for both sides/possible outcomes-Having said that I assume, based on your description, that the combined tax assessment of both "A" & "B" parcels plus combined structure assessments, are similar or equal to that of singleton "C"- if not you could face a higher property tax payment on two properties vs. one. 

Incredibly quiet and exclusive places to live, with Flood Insurance which I don't want.

And it’s all shielded from prying eyes, tucked away in an exclusive community that requires passing through three gates to reach it.

My understanding is that your portion of the profit would be taxable because the exclusion is only for people who lived there.

I'm not sure if this is different from market to market, but should you work exclusively with one commercial broker?

We used to buy REOs almost exclusively, but there just aren't very many bank owned properties.

I work exclusively with investors, so I've always looked for brokers that can support that niche.

Nine states provide general exclusions or deductions for long-term capital gains.