Other than a response of knowing what your comfortable debt level is, how do you decide how much debt to put on a rental property, if any at all?

Learn the system on a local level. 

It seems that if they are a certain level of established that it can be bypassed.

Account Closed, There's a few levels to your scenario.  

But, I don't have a crystal ball so the best I can do is assume some level of inflation of cap rate every year.You will never be 100% right on everything...you can't.

I never made a solid return there compared to the other properties in Toronto, NYC, Minneapolis, Atlanta and New Orleans ... nor has it been conducive on any level to accomplish projects or business initiatives there.

We weren't advised to add luan to level out the flooring and give the peel and stick a level base to start with until we had already started with the LVP. 

Otherwise, for both units, its pretty much new flooring throughout, new kitchen, new bathroom, outside paint job, and restoring porches on both levels. 

As Leo points out, with the leverage you have, at some level of price appreciation your investment will work out ok... but your time horizon needs to be 5-7 years of 2-3k/month if there's disruption in the market.

Otherwise, for both units, its pretty much new flooring throughout, new kitchen, new bathroom, outside paint job, and restoring porches on both levels.