Nothing wrong with a Good financed buyer, and they're likely the majority of your buyers.

But I don't see any major concerns with regards to the cash flow numbers you posted, unless there are hidden expenses (insurance, capex, deferred maintenance, management fees, etc).There is always a risk when inheriting multiple tenants. 

But how do I find out if there is a major problem that I am missing through ignorance?

Most lenders will require you own the property for 12 months before they will allow you to use the new value to pull out cash, before that most will only recognize your purchase price even if you have done major renovations.

You are in the upper part of the country, so you may want to market/list the property inmajor Canadian cities near your subject home (within Craigslist_if available, hospital community boards_ lunch rooms, major & prestigious Universities, and prestigious employer community bulletin boards.) 

This excludes servers, bartenders, etc where the majority of their money is made from tipping.  

I would definitely use a contractor to do the majority, if not all of the work. 

Hi Everyone, Thanks in advance for your advice/comments. 4-Plex for sale near a major university.

Earlier this year we bought two houses that needed major work.

@Curt SmithI'll make a really broad statement, if you do want to do one or two sandwich lease option deals a year it's not a big deal as far as being licensed, this is only my opinion but I think most "departments of real estate" could care less of 1 or 2 dealsThe big point I'm trying to make is if you want to do 50 to 100 of these deals a year, there's no way around not being licensed in most states because you're acting as a major business operation, there is a pattern of similar business activityAnd I've said this over and over, all it takes is for you to get a negative reputation at the department of real estate in your state which will stain your reputation from being licensed in the future; all it takes is one real estate broker to write a letter to the commission and now you've got headachesIt's prudent just to get licensed and build a business you can be proud ofA sidenote:  I think a lot of people on BiggerPockets think that if you are licensed it stops you from doing creative deals,  that's not true at all.Regarding sandwich lease options on nice houses in nice areas, Dodd Frank excludes your relationship with the owner as an investor, if your subleasing and sub optioningI think there's a great opportunity for you getting rent credits and doing creative contracts with your owner as an investor with sandwich lease options, but don't be broke and not have some reserves like 3 to 6 months in case the tenant buyer doesn't pay you when you sub option and subleaseAnother issue is be careful of who you let into the house and make sure the tenant buyers  work on their credit and save money for down payment and they truly want to be homeowners.