Long Term, 1.5 hour or less commuting distance from NYC.My goal is to replace/multiply my current income with REI income.Bigger Pockets:I found BP website on search engine whileresearching/evaluating rentals in NewYork.

Any long distance landlords with advice?

This distance keeps me away from the day-to-day which would make the income as passive as possible, which is what I want.  

The Annapolis area gives us many investment choices within driving distance.

There are multiple pocket parks, an elementary school, coffee shop, market, pizza etc all within walking distance.

The differences in the markets will be like splitting hairs, any potential savings you may gain you will have lost by having a lack of familiarity with the market, lack of contacts and just pure distance between you and your investment.The only people that should be looking to invest in other markets besides their own are those that are priced out of their market.

Rehab from distance is challenging.

An unlicensed broker has time constraints to get an assignment within x days.

Chicago has a great public transit system so check for walking distance to cta/metra, and nearby parks.

I have no ideas if some of these types of software take in account certain aspects or constraints regarding law of legalities in Quebec.