I think looking to get face-time with someone who is experienced in this specific situation and market status would be really helpful to answer some internal questions and provide guidance and external motivation to make a decision and get moving. 

I am definitely not ready for cash deals with a health rehab. 

That is the jist, i would like to add to the responses above that even in the future if you qualify for real estate professional status, those losses cannot offset active income since in the year you generated the losses you were not real estate pro.

I know personally quite few Sec.8 Tenants who drive nice cars (Lexus, Jeep Wrangler), take vacations, enjoy shopping in high end malls......they work for cash and have free health care, food stamps and Sec.8 Housing.These are not legal reasons but that's not what I believe I should do.

Started sending monthly emails back in July/August seeking status updates and was always assured that my taxes were in the que and would be processed in the order received.

It isn't the same as us telling folks where to rent a boat.Michael - Curious what part of taxable status would be affected here.

When factoring in additional costs such as maintenance, property management fees (if you do not opt for a property manager, and you should), and potential vacancy periods, the financial burden could increase.Check this out: If you're breaking even on rent at $1,600, any additional expenses or vacancies directly impact your pocket and mental health.

Not saying this will be true in your case, but always question the status quo!

Until just a few years ago you could retire early and suddenly develop health problems depleting your savings.

With "Condo Status" comes not just increased desirability, but also higher appraisals during refinancing.