Biggest issue would be making sure you are dealing with a reputable company, same as anything else. Apart from that it depends from province to province for what taxes you have to pay. If recovering the GST from out of country is anything like small business remittance, it's like 3 forms and weeks of waiting; hosting provider can probably help you out with that.
The other thing to consider is what you would do with the gear after hosting. If you try to bring it to the US down the road you get hit with import fees again. Who are you talking to for hosting? If you don't mind sharing.
There is a 4% import tax on the gear, and a 14% GST on the hosting costs.
What 4%, I thought it was 5% (inline with GST). I always have to pay the PST and GST where I am so that's a sweet 13% burn, really should have registered as a business. Come to think of it your 14% is a HST I think (Harmonized Sales Tax) which is a bitch in some provinces as you pay extra taxes where you normally wouldn't have before. Sorry drifting off-topic lol.