Its a pain to do any work with tenants in there, don't get me wrong, but it does not need to pass before advertising it for rent.   

It may be painful getting to this point, but once you get there you will be glad you did it. 

I feel your pain; I have also had to battle (at times) with my wife to hold on to my long term rentals!

I am in this too, I have been doing work for some investors oversea and this is the pain falls that I found (time difference is only 3 hours though):- Tenant screening, we found that sometimes without meeting the tenant, everything looked good until the meeting.

You're going to want health insurance and a steady paycheck. 

A property is considered Uninhabitable if "A condition that materially interferes with the tenant's life, health, or safety." 

It's a pain in the butt.

Exactly.Last time I counted, I had 23 business bank accounts, and while it can sometimes be a pain in the butt (for example, I have about 11 different checkbooks), at the end of the year, it makes accounting much, much easier...

I work part time for Costco (their health insurance is unbeatable!)

Which tempts me to tell everyone to put their real estate into S Corps, because you might save on the Health Insurance portion of SS taxes