Frank is right - in Canada you need liability insurance to fly. Even
if you're flying a N-numbered aircraft up there, you'll legally need
liability.

I was able to find out some info from talking to several branches of
the FAA and Transport Canada. I'll first beg the current owner to get
insurance on it and fly it to the states. Otherwise, I'll have to keep
it in Canada, deregister it, get it registered with the US and stick an
N-number on it. Then I'll need a special flight authorization from
Transport Canada to fly to the border and another one from the local
FSDO to fly from the border to my desired airport in the states.

After that, I'll need to get the equivalent of an annual and have a DAR
come out and inspect the plane. He says it should take a 1/2 day and
cost $500+travel. I found out that it had an airworthiness certificate
in the US (for the first 9 hours), so I won't need to have Cessna get
one of its reps to issue an "original" airworthiness cert. The only
thing my A&P will need to do is put together a 337 for the Robertson
STOL and hopefully the DAR will issue a CofA on the spot.

I've been told that when importing to the US, there is no import or
excise tax. Some states will tax the plane, but I believe that this
would happen is you bought a plane in the US as well. If the plane was
being imported to Canada, you'd be paying 7% for PST.

So, the bottom line is that it doesn't look like it will cost much $$
and should be done in a reasonable amount of time as long as any mods
on the aircraft were done correctly and have the supporting docs.

I'll try to post what actually happens here when I get done.

Wish me luck!

Shad