If I'm the buyer and I know you didn't do this work, then what else did you cheap out on?

What are you using for sending Bulk SMS that is cheap but has a high delivery rate?

If you can get a 4 unit and a basement, that would be ideal and create major cash flow and equity creation, plus you can not worry about a property manager and boost your yield.You can get a whole bunch of cheap debt which your tenants will pay down over time, massive appreciation and potential cash flow if you buy right. 

For example I understand your brother is in charge of maintenance, but what if he wants to go super cheap on something that breaks later on and it cost more money.

There are a decent number of VTB's in Winnipeg but it is typically for very cheap properties and/or properties that won't sell. 99% of agents have no clue what they are or how to negotiate the terms of a VTB.Most sellers need the cash for either there next home or retirement so your best chance of finding seller financing options are for buying properties already owned by investors

Good reviews on work.b) Cheap contractor - wants $1,500 for the same work. 

IF you wanted to buy properties on the cheap AND do the work yourself (instead of hiring a contractor), then you want to buy with HML, do the renovations, then do a cash out refi and move into it.

Then I plan on going back to my portfolio lender with 2 town homes and a duplex free and clear to pledge as collateral for around $600,000 in financing so I can go buy some more real estate.If you know what you are doing, this can be a very cheap and convenient source of short term capital.

Mid term and STR is a good option but you will have to furnish it, and do not go on the cheap route from IKEA or something that will break and you will have to replace it again anyway.  

Be a cheap slumlord, and you'll be selling in 6 months.