For instance, a really nice home renting for $2000 you probably won't need to save as much as one renting for $500 because the price of maintaining/repairing a home doesn't differ THAT much (roof is still a roof, maybe if its larger home it'll cost a bit more). 

Do I really need to dig deep and find pieces of crap that need full renovations (I've seen a few of those and they still cost a fortune), BRRRR or some other fancy strategy?

That was just window cost as we installed them ourselves.

Now in the last five years we have a great portfolio and I will be retired at age 60 in costa rica.

Yes they do cost a bit more to form entities but the quality and knowledge they produce is very good in my opinion.

All of them speak confidently of their skills, but are quick to point out that it is quite likely an appeal, etc. would cost a great deal and have limited chance of success particularly in Michigan.

Account Closed is one of them and he might be able to get you a good deal if you still want to invest in Montreal for the other reasons you mention.Alternatively, you might want to really diversify and do the same as I do, which is investing outside of North America in places like the Dominican Republic, Mexico, Costa Rica or Panama.

The items of more value, cost, and the cost as value ascends. 

Bad debt are items that typically depreciate heavily in actual value you could later resale for but sometimes it doesn't matter.I have a massage chair that cost as much as a car.

The probate process will take months to complete anyway and cost a lot of money.