Safety - Learn about Crime Prevention Through Environmental Design (CPTED) and employ the concepts at your property.

What would you do to try to ensure that the PM company is more pro-active in preventing damage to that extent in the future. 

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

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

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.

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.

It's preventing you from buying a deal you shouldn't.You can settle for a bad deal, look in another market where houses are cheaper, or be patient.

Is there a lien I can put on the property to prevent sale until deposit is paid?

This makes it a little easier to prevent the bank from noticing thus enforcing the due on sale clause