Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

My son currently lives in the townhouse b/c he is going to school and works in the area.Since he is young and starting out in life, I would like for him to only cover the basic costs (taxes, HOA, utilities) just enough for me to break even (I believe that will put him slightly little lower than market rent rates). 

If you're heading into retirement, you want to likely get your debt out of the picture.

Their pictures of the leadership team is sketchy as well. 

We don’t know any PMCs to recommend in the Cape Coral/fort Meyers area, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

You can point out spots like nail holes where they hung pictures, dirty spots in the apartment needing cleaning, blown outlets they are overusing, etc.

Do you know of any decent sofas with zippered cushion covers that can be removed to wash?

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

Consult with a qualified tax advisor who understands these limitations and can help develop a comprehensive strategy aligned with your specific situation.Remember: The best tax planning looks beyond immediate deductions to your complete financial picture.

That should cover 2 rental income periods, returning $660 to your pocket.