Welcome to the BP community—it sounds like you're on an exciting path toward financial independence!

Hello everyone: I currently own a long term rental duplex in Bracebridge, Ontario, Canada, which is cottage country and about 20,000 population normally.

NYC is one of the worse cities in the country for landlords.

Oakland scares me, considering renting out my home if I decide to leave the USA for a lower cost of living country in the future, although I know a few people who bought in 2008 renting their homes out in Oakland and doing well. 

You're on the right path—don't overthink it.

I would set a "glide path" to increase rents every 6 months to get closer to the market).

Gabriel, I work and educate investors nationwide but I do have to say - CT is one of the most tightly-knit investing communities in the country.

I have done my due diligence and I have made my own calculations and just looking to confirm that I am on the right path. 

I learned something from these deals, but I am starting to think the path could look different for some investors getting started.Too many new investors try to be too hands-on when they don't have the time.

This is a false statement that leads @Neal Coppola down a false path of belief.