It is the equivalent of crashing your car then trying to buy insurance to fix the car after the fact.A home warranty or homeowners insurance policy will not pay for mold because mold is a maintenance issue.You didn't say what is wrong with the garage - if it's a broken door opener that is typically covered on a home warranty.My experience is mixed with home warranties and I can 100% tell you your satisfaction comes down to the local trade person that shows up.The home warranty company does not employ trades - they contract them locally at a fixed rate for the work performed sort of like how car mechanics are paid. 

Id speak to a local attorney to get a proper contract set up 

Make sure tenants know what these terms mean and that you're following local rules.

We've got a national bank, a local credit union, and a direct-to commercial mortgage backed security.

Talk to some local property mangers to get a feel for rental prices and demand.

Yeah, I'm going to stay local in St.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Does anyone know of any local Winnipeg meet ups or online Canadian Real Estate communities?

Read books, take online courses, and join local real estate investment groups.

Even facebook might have some good local groups for you.