I'm currently invested in executive rentals in Burlington and have previously owned multi-family in Hamilton which I have since sold.

Have a couple of executable exit strategies for the "just in case scenario" and the risk is still acceptable to you.

Contracts have already been executed and you signed individually?

If MSFT is up 22% in 3 months and I have a limit sell order in place that executes when MSFT hits 25%, I'm more willing to lock in my return on MSFT while letting my T ride longer even if T happens to be down a couple % over 3 months because I know that T trades within a certain range, and I don't mind waiting a little longer while I collect T's higher dividend. 

Either way, you will likely need to come to the table with at least enough cash for the repairs + contingency buffer unless you find carefree friend/relative private money or a partner who is hands off and relying on your skills and time to execute the project.Best of luck!!

You have a plan in place and you execute.

Unless you are planning on assigning--then you'll need to be property executing the contract to be able to assign and the 2-T is inherently not assignable and requires agreement to specifically assign.So, there's more to it than first meets the eye. 

In the event they wish to go month to month or renew multi-year as opposed to the automatic one year renewal in the lease, should we execute a brand new lease or is it better to do a modification / addendum of sorts to the existing lease simply outlining everything is still in full force and effect and we are simply changing the length of the lease? 

In securities they refer to this as the 'prudent investor' rule.Keep an open dialogue and communicate with your 'lenders'...through good and especially if the ride gets a little rough.Do select and utilize a qualified third party servicer to execute the terms and conditions of your lending agreement. 

client has offered to provide for my safe keeping an executed Quit Claim Deed as added security. ( not worth the paper if I am not first position I think?)