The downstairs is a small grocery bringing in $1000 per month with a scheduled $100 increase each year until it reaches $1300.

@Anastasia Kristina I found a few markets in Ontario and Quebec that have great cash flow, good and constant increases in property value while being stable markets (low vacancy, high rent to purchase ratios, above average population growth).I like Outaouais, Laurentides, Lanaudieres, Estrie and certain pockets of Montreal in Quebec.

Causing my operating expenses to increase, stripping my already tight $100/month cash flow. 

If current Hoa fee plus double the increase monthly Hoa fee is a number you can live with, go for it.

Provide the lawn mower and snow blower, increase rent or add fee.2.

Raising the rent $75 per month, per year, every year is damn steep increase.

You can always find ways to increase your income, but not your time. 

Not a big business but still we take care of both sides properly to avoid turn over rates to increase more return to the owners by taking care of tenants quickly and rightly.

You will increase your cash flow investing in multi unit purpose built properties and will likely be looking at a commercial mortgage.Purpose built multi unit rentals is you best option to grow your investments and your income. 

Given I'm looking for buy and hold for over 10 years would you recommend this deal as good deal.If I assume conservative 1% appreciation and 2% rent increase, I get around overall 9.5% return over 10 years.