Rochelle, Heat is a necessity and AC is a convenience.

My reply was that he pay online through the tenant website as it is a condition of our lease agreement, its convenient, safe, yada yada.

., please read that sentence again. you need to sell "a different type of home"...probably you could cable-ready your place with one of the cable technicians that "moonlights"you could change some of your power outlets to the usb-charging-type....conveniently placed....one con of you providing internet: do you keep logs for when they download the wrong stuff???

Convenience is a big factor in RE, so cash for keys is a very common procedure.

While I'd never buy a super expensive car (I have a long ago paid-for 2008 Mini Cooper S that's fast, fun and perfect for me), I bought a pretty expensive house but I can walk everywhere, can rent my basement apartment for 3/4 of my mortgage, and love my pretty, convenient, city neighborhood.

I have to agree with @Roy N.. i provide free Internet myself to my student rentals ( i also control the thermostat and door locks if i have to, from my house - which includes changing the door code with new students, front door only) its a convenience for them and me and helps rent it. as for my other properties i do not provide that service, the tenants pay for that service themselves.

The "convenience" of having her help with YOUR mortgage when you're not even sure this will go anywhere will turn hugely inconvenient quickly.

That being said the challenges related to this property have to do with convenience.  

One catch that may come up is if the the HOA is ever caught in litigation, this may hamper your ability to unload the condo at your convenience - it deters buyers and banks.  

Give her a notice something like this:Dear Tenant:I'm sorry we haven't been able to find a time that would be convenient for both of us to do the maintenance work that needs to be done in the bathroom.