I can speak for the US side of things. Not sure exactly how Canada handles "foreign source income" but there is a tax treaty between the US and Canada which should eliminate most chances of double taxation.
We are hoping to sell our house here this summer, though it didn't sell last summer....my biggest question is if I sell after 'landing' do I have to pay canadian taxes on the sale (or profit if any from it), or is it a USA taxable event?
Because the house is located in the US, it's the US that takes precedence (and the state where the house is located). If you sell after your move, you'll probably have to file a "non-resident" return for the state where the property is located.
Finding a firm in Toronto would be good, as we drive through all the time to get to our farm.
I did google, but most firms deal with 'Big' corp's and want min 3000 bucks to give advice...
Before forking over too much money to a "tax advisor" check to see if there is an IRS office at the Toronto US Consulate. The consulates normally put out some good information on taxes for US citizens living in the country - and it's free!
The IRA question is most important, I'm unemployed right now (software engineer) and drawing from it a little to pay bills and will probably through this year. Do I have to pay taxes in Canada on the withdraws? Or just US taxes? If I put off 'landing' till June does it make a difference?
You'll have to pay all the US taxes on any premature withdrawals (i.e. regular income tax plus the early withdrawal penalty). As a US citizen, you're going to have to file US taxes no matter where you live in the world. And anytime you take money out of your IRA, you owe taxes first to the US (since the money was tax exempt when you put it in the IRA).
Thanks to the tax treaty, though, Canada won't tax it again. You'll have to check with a Canadian tax preparer to find out exactly how to declare your IRA withdrawals so as not to be doubled taxed, but it shouldn't be a terribly difficult thing to do.
I've heard rumors that there is a Canadian branch (or maybe just equivalent) of H&R Block. That may well be all you need. The US side of things seems complicated at first, but once you've been through it a time or two it should go pretty quickly.
Just remember that you can't add anything to your IRA unless you have taxable US income that is considered "earned" (i.e. salary), so for most folks living outside the US, your IRA is pretty well frozen once you change residence.
Cheers,
Bev