She was also a pain on her move out and stayed 10 days past her move out date, because her loan fell through on her other house putting me in an awkward place with the next tenants.

At the time, it was a pain in...

With real estate, you maintain much more decisionmaking control and although we experienced a wicked housing collapse last decade, many real estate investors can still argue they maintained cashflow and that their respective market didn't feel the same pain others did.The knocks I would have against real estate is it is significantly less liquid and the fees are much higher when it comes to buying, selling and financing.With the introduction of Robin Hood, it's a race to the bottom as brokerages have been slashing trading fees in recent years.In my mind, there is nothing more passive than buy and hold stock ownership, though you may be relying more on capital appreciation, whereas many real estate investors prefer passive cashflow.

Depends on the deductions.I had several MF's and some years back before ObamaCare, when I quit my corporate job, I bought my own health insurance , about $1,500/month which I couldn't deduct.

FHA is a pain for the seller.  

I have Life/Health insurance licenses.My ultimate goal is to have more time for my family by leaving the 9-5.

Therefore, since you are not being "bettered," you have not received income.However, emotional damages like pain and suffering are usually considered taxable since they are not physical injuries.

I understand Cleveland is a pain when it comes to water, sewer, trash and has o be in the owner's name. 

One of my brothers is not open to this idea and as I have had health issues, have lacked the energy to really pursue a conversation about why he feels this way.

(a) A landlord shall:(1) comply with the requirements of applicable building and housing codes materially affecting health and safety;(2) make all repairs and do whatever is necessary to put and keep the premises in a habitable condition;(3) keep all common areas of the premises in a clean and safe condition;(4) maintain in good and safe working order and condition all electrical, plumbing, sanitary, heating, ventilating, air-conditioning, and other facilities and appliances, including elevators, supplied or required to be supplied by the landlord;(5) provide and maintain appropriate receptacles and conveniences for the removal of garbage, rubbish, and other waste incidental to the occupancy of the dwelling unit and arrange for their removal; and(6) supply running water and reasonable amounts of hot water at all times and reasonable heat except where the building that includes the dwelling unit is not required by law to be equipped for that purpose, or the dwelling unit is so constructed that heat or hot water is generated by an installation within the exclusive control of the tenant and supplied by a direct public utility connection.