What is my ideal scenario from the eyes of more experienced investors?

These are old buildings so the plumbing is probably not a direct run from the basement, so I would ideally need to measure water in at the point of use.  

If your tenants are the kind that can set up the repair themselves, that's ideal because then you aren't some middleman trying to schedule.

Ideally I would like a multi-family dwelling priced around $250k CAN with a sizable cash-flow at 5% down - though wouldn't we all.

If they allow you to pay them back at the end of the project with Jo payments in between that would be ideal. 

Ideally, you should consult an attorney who does this. 

The school is great, location is ideal for people who want a small town life without being to far from the city needs (Fort Wayne,IN).

One fix to control heating / cooling costs I've implemented is lockbox around the only thermostat in the property (not ideal). 

State requires you accept paper checks)Simple to use Maintenance requests so they stop sending post-it notes with the rent.The ability shut off payments, or even better block partial payments, in the case of rent arrearsNice to haves are:The ability to securely share documentsBlocking Partial PaymentsNon-ACH online payments, ideally without having any additional setup on my side.I already do all my accounting in a properly double-booked accounting system, so that isn't a priority. 

But my ideal rental is 4 bedrooms, 2 or 3 baths near metro stations.