Chances are he can't afford the rent and will eventually start making unnecessary repairs in order to pay $0 in rent.

@Fremy RossoEMD is due at the time of contract execution.The LLC sale is cool and works well for savy investors but it is totally unnecessary and comes with its own set of hurdles.Our EMD is $10 on our sales agreements because we represent ourselves correctly to the sellers.

As  I recall, I don't think any of the brokers or their websites prevented anyone from selling their investments for months. 

If you don't have healthy trustful relationships with everybody you are working with you run the risk of dealing with unnecessary challenges that usually have nothing to do with Real Estate.

Does the condo association have enough reserves to prevent future jumps in fees?

I would do a little research as a large number of them are just venues for guru's and pitchmen to sell their class, software, or mentor-ship, all of which is probably unnecessary for you to get.

We put pad locks on our gates to prevent them from coming back in without us being there.Finally his friend contacted us about signing a lease.

Also, the MRI was unnecessary, he has mechanical back pain from lack of movement and poor posture and needs PT, chiropractic, massage and regular exercise (preferably including yoga, not high impact until he is doing better).

Our priorities are 1- fixes for safety or to prevent further damage; 2- fixes that improve the rental income or will draw great tenants (we're turning the studio to a 1Br to increase rent), and 3-things my wife wants for customization/aesthetics (happy wife, happy life).Some specific questions I had so far are:1) We have a modified bitumen roof. 

This seems common sense but it prevents bad landlords from purposefully leaving it empty for the entirety of the lease and claiming the old tenant owes the entire lease amount.