So far, by doing little extra upgrades I've managed to routinely attract quality tenants and haven't had to replace carpet anywhere.

Besides loss of control over when and how you make capital and routine maintenance expenditures, there's additional insurance you need to consider.For example, if someone seriously injures themselves within a common area, and the judgement is over whatever liability the association carries, YOU will get assessed your share of the extra dough.

I don't want to sound cynical, but I know of ownerswho charge less on the late fee (in your example, say, $25 - $35)and then expect to collect it in many cases.Set it too high, and people will really try to pay on time.Set it just right, and people will routinely pay late, andyou collect the fees.

I brushed off the idea because I was uncomfortable dealing with the elderly.

If you feel a little uncomfortable - then adjust by a little.  

They may have been talking about the reinvestment requirements in generally where you must reinvest the Net Sale Price (Gross Sale Price less certainly routine selling expenses) and not just the net equity or net proceeds. 

You will need to get uncomfortable if you want to make it in this game.

I have had to paint my siding due to graffiti spray on it before and I routinely pick up baggies alcohol bottles and drug paraphernalia in the yard when I mow the grass .

Which was also very uncomfortable. 

I knew what I had to do each night at work: I'm a man of checklist routines, patterns, and structure.