I did most of that trip recently in a Zenair 250 and really enjoyed it. I've only got a few hundred hours myself and I've only done the trip a few times but hopefully you find this useful.
Between Regina and Vancouver the winds are usually from the west or north west. My home base is Calgary so I've done Calgary to vancouver and Calgary to Regina in separate trips.
When flying from Calgary to Regina I can usually make it non stop unless I have a headwind.
Regina to Calgary usually ends up with a headwind so I plan a stop in Medicine Hat (CYXH). It adds just a few miles to the trip. Bar XH has an excellent facility and outstanding ramp service. From there plan direct to Springbank (CYBW). This leg will be about 450 miles. You need a Regina VNC, Calgary VNC and a Calgary VTA. Calgary airspace changed this year so you need current charts. Springbank can be very very busy as there are a lot of students training there. If you're on a flight plan you shouldn't have problems getting permission to enter their airspace. If you radio the tower and they don't answer just wait a minute and call again. They're not answering because they're too busy to let you into the class C so just orbit. The entry and exit procedures for springbank can be found in the CFS, the Priddis Corner entry would work best for you.
If you're planning to overnight in Calgary let me know and I can suggest other local airports, places to stay and things to do.
The next leg I recommend would be to Salmon Arm. John has a great facility there and an airport car if you want to run into town. Plan about 2.5 hours. Best plan is to follow the TransCanada. 8500 feet works good but at 10,500 you can cut a few corners. Great sightseeing along the way. If you run into problems you have golden, revelstoke and Banff (grass and emergencies only).
It's not uncommon to find that the pass between banff and salmon arm will be fogged in or have low ceilings. Leave yourself some extra days to get through as it's hard to predict. Talk to the Calgary Flying Club about a mountain checkout and some more local experience. I think you can do the pass as low as 6500 feet but I like to fly high and have never worried about it.
Salmon Arm to Vancouver is a casual trip msot of the way and can be done without having to climb high or worry about narrow passes. Very relaxing until you get to chilliwack and then it will get very busy. There's several airports you have to fly over and staying at the right altitude is important. Check in with Center before you get to Chilliwack and then get handoffs the rest of the way. Boundary Bay is your best choice as it's close to vancouver with good access. There's also a recreational airport just a few miles to the east along the bay (closer to white rock).
This leg is where you will benefit from having a passenger to watch for traffic and spot airports to help you follow on the map. You need the Vancouver VNC and Vancouver VTA. The VTA shows the entry procedures for Boundary Bay. Expect a lot of training flights. I don't want to make this sound overwhelming, but at the same time don't expect you'll have time to flip throught the CFS looking for airport information or frequencies.
Departing Vancouver is much easier. some suggestions on the way home are Kamloops or Kelowna as a stopover or you can head to Cranbrook and then follow the crowsnest pass to Pincher Creek. I did that in an ultralight a few years ago and it's a fantastic trip.
Once you get through the pass to Pincher Creek it's an easy trip all the way home. If you want to stop over Lethbridge is a good city to overnight in with good taxi access. AirWest on the south end of the field is a good place to tie down and fuel. Don't use the main terminal as you may be charged fees for using it and there's no overnight parking there.
Some other useful information would be to get a SPOT with the tracking feature enabled. Share the webpage with your friends and leave it on the dash of the plane. Invest in a good winter survival kit and throw in a sleeping bag if you have room. Technically you can do this trip in a day but you'll be exhausted. You want to leave Calgary early morning when the winds are calmer and so you're not staring into the sun flying into Vancouver. Go to Google Maps and track a course from Chilliwack to Boundary Bay. the maps are detailed enough that you can identify the ground features and airports.
Have a good trip.