I am originally from the states and not sure if it's worth buying a property here (I am concerned about labor costs for maintenance) or should I do a house flip since there are some opportunities in Alberta (Calgary primarily).  

Too many people will just use a % of rents for things like maintenance and capex.

My thought is that since I am already wanting to learn the in’s and outs of property management and really involving myself in real life experience, perhaps if I offered to take care of the whole property for him in terms of dealing with the downstairs tenants, scheduling repairs/maintenance, and keeping up the properties landscaping so that the investor can remain more hands off he might be willing to give us a break on the rent so that we can save even just a little bit extra each month.

Its a great tool to use to calculate your various amounts, mortgage, prop taxes, amounts to save for repairs and maintenance. 

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Foundation repairs comes with a lot of other hidden costs and damages (pipe damage, lawn maintenance, sprinkler system repair, floor repair.) etc.

I can tell he's kind of high maintenance and a bit of a pain. 

Its sort of a good thing since they can be used when you sell to offset gains or in some cases the depreciation unrecapture.Talking of equity growth, here is a recent discussion that covers an important topic that is routinely glossed over in BP in favor of cash flow:  https://www.biggerpockets.com/... 

Tenants pay water/sewer/yard maintenance/trash/electrical.

The pros of condo rentals is that you don't have to handle/pay for exterior maintenance or lawn care (outside of your dues).