Detroit is not a market to play around in without a professional on your side.Remember: cheaper doesn't mean you'll make more money.Start by going to www.narpm.org to search their directory of managers.

My initial question, does anyone know what's involved to invest in a US market as Canadians?

The banks are just very conservative in this environment.I met a gentlemen who came into my brewery (current location that I lease) and we got to talking about the general market and our plans to scale. 

The RE market is a semi efficient market.  

I am sure, alas one cannot specialize in all markets:)

The market appreciates 3% per year.Pay cash for one house and rent it for $1,500.

Once the rental home is sold, my half of the proceeds will be roughly $113,000 (this is after closing costs and taxes and is an estimation based on the current market value). 

I'm grandfathered in to the lower pricing of the past (was originally like $850 for their top plan, and I had 36k a month plan) - and they allowed me to add an additional market (which adds additional 36k a month) for a discounted rate.

I work heavily within the Asheville market and would love to connect with you and learn more about your investments. 

The next best time is when you decided you want/need to sell it for business reasons: current market is favorable, you have a better investment opportunity, you have an offer you can't refuse, and so on.The worst time to sell is when you were waiting to sell due to tax considerations, and now you can't sell anymore.