Welcome to Orchid Board.
Personaly I find Phalaenopsis to be the easiest... but it can all depend on your condtions and some people find them difficult in their conditions.
Posting a picture here would be a great help as then people can advise if it does need repotting or not.
What is it potted in now, I think Tucker has asked some good questions along these lines and that would help.
Here are a few repotting tips regardless of what it is potted in now...
1. Always get the best quality medium you can. I almost killed several by just using the stuff labled 'orchid compost' in my local store. I would now always advise getting it from an orchid specialist... not sure the best for you in Canada but
rePotme Orchid Supplies is meant to be good (I'm in the UK so use a closer one).
2. Remove all the old medium and wash the roots. Unlike repotting other house plants you don't leave the old medium and just add new arround the outside, the main reason for repotting is not to increase the pot size but to replace the old medium with fresh. As a rough guide, if it's potted in moss it needs replacing every year, if it's potted in bark it needs replacing every two years.
3. Cut away any hollow or mushy roots when you repot.
4. Choose a new pot which can JUST fit in the roots. This may be larger than the old pot or it may be smaller (or it may go back in the old pot). Until you get it out and see what roots you have it can be difficult to tell which it's going to be. If a lot have been removed then it will need to go smaller, if none have been removed but a lot have grown it may be impossible to get back in the same pot. Again the point of repotting with orchids is generally to give them fresh medium not to change the pot size, a change in pot size may be needed as well but that is more of a side consideration. It is better to have a small pot that fits the roots even if it's then top heavy as you can always use a heavy empty outer pot to balance, but a pot which is too big can easily lead to rooten roots.
5. I favour clear plastic pots because then you can see the roots and easily judge when it needs watering (when the roots all the way down turn silvery). Others prefer other types of pot though and there are other methods of judging watering.