If you're married, you'll likely be attach posted to wherever your wife is to wait on OJT (on the job "training") after completing Basic Officer Training until flight training starts. I have never heard of anyone with dependents not returning to their family while on OJT (other than by request).
Your Phase 1 (primary flight training) should only take 3 months. It may be longer but you will go on this training by yourself. After completing PFT you'll return to where your OJT was. If you're not married or just want to try a different place to see another flying community you may have an opportunity to do OJT at a different Squadron but you will have to arrange this with the receiving Sqn and pay for all moving costs on your own. It's not a bad idea to see different Sqn's and different aircraft types before you're asked what your preferences are.
You can bring your wife to phase 2 (basic flight training) in Moose Jaw. It's worth considering whether to bring your wife to MJ or not. The community is a small town with little in the way of recreation or employment opportunities. For many guys, leaving their wife back home (where OJT was done) and attending MJ on "Imposed Restriction" is a better way to go and not uncommon. This means you're restricted from moving your family and all your stuff. Generally, this IR is requested so you're asking for a restriction to be imposed on you but that's all semantics. MJ should take 5 to 7 months. But lately there have been delays and it's not uncommon to be on course for a year or more. While on IR, your rent and meals are free and you'll get separation allowance (I think about $300 a month) as well as Leave Travel Assistance - depending on the distance to your next of kin, it's about $500 to Vancouver for example, to travel back home once a year. You can also use it to bring your spouse out to visit you in MJ (reverse LTA).
If you're on IR, after you complete MJ you'll go back to your spouse to do OJT until phase 3 on Multi's or Helo's. If you have brought your wife to MJ, you'll do your OJT there. The wait could be anywhere from a month to up to 8 months, depending on the state of the training system at that time. When you go on Ph3, you must leave your family wherever it is, and like Ph1, go solo. Ph3 should take about 6 months on multi or helo but again it's not uncommon for it to take longer. Once you have wings it takes about a month to get fully posted out of MJ and sent to your new Sqn. At this point you get a full blown all inclusive move and typically you bring your wife to wherever you're going. IR is rarely done at this point.
As mentioned before, if you are selected to fly jets, you'll stay in MJ and continue your ph3 there, get wings and then either be posted to MJ to instruct or sent to Cold Lake for more training. If you want jets, this may influence your decision to bring your wife as your life will be on the prairies for a few more years - if not a few decades. However, peoples' preferences change dramatically sometimes once they start Ph2 and get a taste of what's to come.
Your wife can come and visit you in MJ and Portage - stay in your room in the Barracks and eat at the mess. No problem at all. If she starts to camp out in your room for months on end, someone will probably have a problem. But a visit for 2 weeks or more hasn't been any problem for past courses. There is very little opportunity in Portage and you won't be there very long so although you could put her up in an apartment (or live in one yourself with her) the time frame is so short it's not worth it. I can't speak to the opportunities in MJ but I would guess that unless she's a nurse/doctor/school teacher, the only thing available will be Walmart or Tim Hortons. Rent in the PMQ's in MJ is cheap but there's a long wait list to get one. I have heard from students there now that renting in MJ is difficult and not that cheap.
In some ways being in the training system is very hard on a family. You're gone on course for up to a year (maybe more) but you don't get many of the benefits of a guy who would deploy (and generally not deploy for that long). Although you can visit your wife or vice versa, other than Ph1, training is pretty intense and you have little time for visits. If you do move your family to MJ, it's a Orderly Room move (not a IRP move) so you're not entitled to many of the things that a full move gives you. I don't know what the differences are but you can easily find them on here. You're expected to be ready to go on course at any time (and should be) and expected to perform every day on course. Once you're done training, you go to a Sqn where there is typically more focus on quality of life concerns and you're cut some slack for family considerations. You're stable, posted to one location for a period of time and have a little bit of certainty.
In training, you have no idea what direction your career will take, where you will ultimately live, opportunities for your spouse etc. Generally, guys in training are also unfortunately fed predicted course dates but these are rarely accurate and they aren't told a realistic time frame for their next course. This is difficult because if you're going on course for 8 months starting in a month you need to get ready and get your wife/kids/house ready for moving or you being away for 8 months. If that gets pushed ahead continuously by 6 weeks - for another year - you're constantly spring loaded to go, but never told the real story until the last minute.
All I can say is you need to have your ducks in order and your wife needs to be ready and understand. If she has a good job going right now and/or a good support network of friends or family where you are now, I would discuss with her and give thought to leaving her there. She'll miss you in MJ, but she'll have support. You will be pretty busy in MJ and not have much time for her anyway. It gets better when you're on Sqn and a bit settled.