Above all how do you see your employment and income growth over the next 10 years.

I realize I’m all over the place at the moment and trying to hone in on a focused strategy to achieve my goals; the goals being to generate cash flow, wealth accumulation for financial freedom.

From what I know, which is not that much, it's tough to generate high cash on cash returns on condos especially when the avg price is around 500k now in Ontario.

Generally we'll research population, job, and employment trends first and foremost.

Only to find that they didn't generate enough cash in the sale to pay the tax!

San Diego investors -- I'm currently working on my first home renovation, employing a live-in flip or long term flip.

I'm self employed you just have to eat paying more in taxes or make more lol.

We have a few retired military friends who have moved dozens of times in their career and employed a strategy such as the one above.

Flipping would increase your taxes because you have new self-employment taxes to pay, if you didn't use some tax mitigation strategy.Big picture observation: your taxes shouldn’t have increased just because you bought these rentals (unless these rentals gave you huge positive cash flow even after depreciation during the first year). 

I take it that means you're self employed?