In my opinion, Windsor is the place to be right now; low housing prices, high rents, demand far exceeding supply, and multiple catalysts including 2 major bridge projects (thousands of well-paying jobs for 7-10 year duration of the project), revitalization of downtown core, revitalization of Detroit, and investors from all over Canada flocking here to eat up already limited supply. 

With so many variables - I just want know if this is a good deal at its core or am I  biting off more than I can chew ? 

Most people can't source profitable properties and contractors in-market let alone out of the country.Tons of profitable strategies in real estate investing...OOC BRRRR can be done but I suspect it's highly uncommon.No kidding I cringe every time I read a post on BP with someone who has never done a OOS rehab and is looking for their core 4.. great in theory highly risky in practice..

I tell people we don't because 1) it's not our core competency, and 2) I don't mind a win/win.  

I know people who rent out luxury rentals one to 2 months a year for ~$120k or so a month.But I would always want that core home to come back to as my base of operations so to speak. 

If you invest in D.C. area you are banking on appreciation of the property and rent growth, it’s basically impossible to find positive cash flow in our main core, as you go farther out from the city you can maybe break even or make a little.

Invest in the city core. 

Don't buy in the roughest neighborhood in the urban core.

What is the best way to learn, start a business, make connections and build my core four in real estate? 

The note investing industry is very mature in the conventional mortgage sector, but I have yet to see opportunities to purchase non-performing, short-term, high-interest debt provided to investors.As we're growing, I've raised more capital, so I figured this could be an effective way to deploy that capital within my core competency.