I like the strategy of doing evals 2 times per year that allow the tenant to pay for any damages they've caused so you're not having to ask for it at the end.

Anything more than that causes real problems with cash flow. 

The line in your original post "I'm a first time investor" would cause me to recommend you not taking on a project of this magnitude until you have some experience.This could work out great or it could be a huge money pit.

Kitchener is very diverse employment market and has a lot of growth coming with a new google building being built downtown near wellington and King street. kitchener is better than Waterloo since Waterloo has a rental bylaw that causes extra expenses and grief for landlords in Waterloo.

I agree you will make more selling individually, but it may not be worth the time, and the issues it causes for a potential 1031.

I would recommend having a new lease drawn up for you and the tenant and clear up the language that is causing the confusion. 

@Jaysen Medhurst it’s only one other unit and yea it might not be worth it cause I was pricing them and they are a bit spendy thanks

There are many reasons that can cause a tenant not to be able to pay the rent. 

I don’t know the courts well enough to know if there is any one or a combination of an older seller, potential for loan being seen as a personal/consumer loan and the rate of return would be enough to cause this deal to be completely dismissed as a consumer loan if I had to bring it to court for non-performance.Thanks in advance for any thoughts.

by February 15th (or around that date since Feb had 29 days).Its now March 2nd.And now that my timing is off, I'm confused about what will happen to their lease end/move-out date: I had to give them 30 days notice before the end of the lease and not having done so will cause them to occupy the unit past their original lease end date (March 15th).Additionally, if I understand the wording of my lease correctly, if tenant remains in unit after lease ends and without renewing the lease, the "lease" defaults to a month to month...Exact timeline for everything is clearly confusing to me since I missed the date for sending a lease-termination notice...