[tpm] Cross-border contracting

[arocker at Vex.Net]

Caution; IANAL, I just inspire the same affection in other people.

>
> 1. Should I incorporate?
>

Yes. It's worth incorporating anyway, as it's easier to keep
tax-deductible expenses separated from personal ones, allows for planning
of payments to suit tax-timing, and other good things. The only annual
cost is the trouble of filing accounts with the CRA, which you can do by
hand if you keep things simple.

Incorporation is not expensive; I did all my incorporation paperwork
myself. The only reason I can imagine to involve a writmonger is that you
expect to involve other people in the company.

It also allows you to say, truthfully, "Business. My company is sending me
to talk to Acme Corporation (or whoever the client is)" when asked the
reason for your trip at the border.

> 2. Is it true that I can operate a sole proprietorship in my own name
> without needing to register anything?

Yes. (Whether or not there's any cross-border work involved.)

> 3. Will I need to charge the customer (who is American) HST?

I'm pretty sure the answer is no, especially if you (or your corporation)
are under the annual cut-off, ($30k last time I looked). Consult an
accountant if you're worried.

> 4. Is there a preferred method of payment?
>
Unmarked, small denomination bills in a brown envelope? A US $ account
with a Canadian bank having a US presence, (e.g. TD) might be a good
solution. Ask them, or your bank. They shouldn't charge a prospective mark
for the advice.

> 5. Do I need insurance?

I'd recommend travel sickness insurance, if you're going to visit the US.
Trivial $/yr, unless you have some nasty complaint. Deductible, of course.

> 6. Are there any tax gotchas I need to watch out for?

Don't know for sure, but I can't imagine any. Just keep good records.

> 7. Do you have any other advice and/or pointers to resources?

Look into getting a TN-1 visa; it'll make crossing the border much easier.
http://travel.state.gov/visa/temp/types/types_1274.html Just don't mention
"programmer" - "systems analyst" is better. This is where legal advice
would probably be helpful. The more "official" the initial US client is,
the better your chances; FBI/NSA/CIA or the DHS itself would be perfect.

Don't EVER tell a US Federal official anything you can't reasonably
demonstrate is true; lying to a park ranger can get you barred from the US
for life.