As far as following up with the owners would you recommend to go and talk to them directly or regularly send them flyers and marketing materials (recently sold brochures, market reports etc...) to keep in touch with them? 

Directly south of town and jack britt are most competitive, but not necessarily better deals.

If you would like to discuss this further please feel free to reach out to me directly.

Is there anyone with experience with this, and can point me in the right direction?

Alternatively, my more specific is Malden and Everett which has direct access to trains and buses and you can find 2 families for the same price range and an occasional three family with work needed.

A new smaller furnace and AC unit outside costs around $3400 (direct cost...I just got one). 

@Nathan PlatterThe short answer is No, your friend cannot directly invest in U.S.A. real estate from within his RRSP.A self-directed RSP, with some restrictions, may write notes and hold mortgages for real property in Canada, but it cannot own property itself.FYI for Omar as well.

They'll collect your email and phone number and send you deals directly.If you want to take a direct approach to getting deals on your own, you could get in direct contact with homeowners who are interested in selling their home but haven't listed the house for sale yet.

The LLC investment, not a direct real estate investment, was made by your IRA  - and that LLC still exists.

Direct quote from HUD.gov, stating that owners and managers may set reasonable occupancy limits outside governmental limits.