Thanks for sharing your house hack experience, I did it whilst living in the UK, I believe we should all do it at least once, to gain a bit more experience of land lording and managing tenants.Good luck!

@Anthony Dooley the problem is not getting people to say yes the problem is getting someone to say yes who wants out of real estate and are willing to accept a large capital gains tax and depreciation recapture from prior exchanges on a 10+ million dollar property.

It has also increased in value by 20%; therefore cost basis has reduced and capital gains exist.I clearly understand I need to pay transfer tax.

They aren't purposely charging you (the money goes directly to FHA, so it's no gain for them).

Or try to find somewhere we can stay temporarily like a long term hotel or month to month apartment (pricey and defeats the purpose of gaining cash flow) until we find another more suitable home? 

@Rex Celle, I'm not quite as formal as a dedicated PPT (just jotted down in my notebook), but yes.I haven't really adjusted my 3, 5, 10-year goals, but have adjusted how I plan to get there as I gain knowledge, experience, and insight.

My thought is to sell and to reinvest the gains, possibly in an opportunity fund to avoid capital gain taxes. 

I have family who have gone down this road with "handshake agreements" that turn into issues when the $100,000 gift/loan to buy a property in Boulder suddenly turns into a $500,000 gain in a few years and no one knows who is owed what. 

I've been trying to research Ontarios capital gains taxes and it sounds like as long as I live in it during the calendar year as my primary residence I'd be exempt from the tax, so long as it isn't a pattern and the CRA can't say that it was done for income reasons.

If I need to put money in to get money out, what have I gained?