Hello!
I live in Winnipeg, and yes, many people do indeed think it's boring, cold, dangerous, but I have lived here for 17 years in the south end and one year in the north end and I think the south end is a good place to live and I've been used to the weather. I was raised here with my sister and parents in a middle to upper middle class area. As far as schools go, I have been to about 6 from kindergarten to grade 12 and I have liked all except one. In these schools there was hardly any bullying, it wasn't that hard to make friends, and a lot of people liked the teachers. My high school in the north end was actually pretty good too but the area around where I actually lived was not so safe and not very comfortable and both my boyfriend and his sister had been mugged within a year..
In the south I live in a quiet and beautiful street. Not a lot of crime goes on near here... no gangs or anything. Of course no area of a city is completely crimeless.. like there are occasional thefts so people just need to have common sense and lock up their doors. (One time we had stuff stolen from the garage but my dad hadn't locked up.. so that's his fault)
On nice sunny days in summer and fall I love going bike riding or going for walks here and it feels safe. There's a really nice park called Kings Park somewhat near my house and a lot of people take their family and/or their dogs and walk around the long path near the river.
There aren't any really THRILLING things to do in Winnipeg, like there is no awesome amusement park with rollercoasters of course. The Red River ex comes to Winnipeg once a year and has some thrilling rides, and one rollercoaster. I used to go to that but honestly sometimes you'd have to wait like half an hour to get on a ride and it ends up not being worth it to go.
What I like doing here in Wpg besides biking (in late spring, during summer, and early fall of course) is going to the Forks, to me it's a unique place which can be nice in summer and winter. In summer you can go for boat rides and stuff on the river and in winter you can skate and it feels Christmasy. There are lots of shops, and different kinds of foods. Magicians come there, artists, there are firework displays on holidays. I also like going to comedy clubs and stuff. I think the site you mentioned is great for seeing the things there are to do. There really is quite a lot. And sometimes I search through the magazine here that shows what leisure activities you can sign up for, and what your kids can go into. There's dance, sports, music lessons, language lessons. There's a mag here called Where magazine that has information on what a person can do while in Wpg. It's good to search around as much as you can!
As far as houses go, in the more decent areas of the city you can buy a 4 bedroom house as low as $135,000 or so(not likely it will be over 1000 sq. ft though!) There are houses with 4 bedrooms though in good areas that are 1200 or so sq. ft. for about $165,000. (You can check listings on mls.ca, you can choose Winnipeg and then each area, I chose South West and these figures showed up. ) You can also check for houses in Regina there.
For wages, all I can give are sites, I often look on the net to check out things like salaries for jobs.
http://www.payscale.com/research/CA/State=Manitoba/Salary
^That is a site which is updated often... You can actually view median salaries by city, you can view by job, etc...
http://www.payscale.com/research/CA/State=Manitoba/Salary/by_City
For Regina too:
http://www.payscale.com/research/CA/City=Regina/Salary/by_Practice_Area
You can scroll down to view other charts..
As for weather... well I'm sure Regina and Winnipeg can't be much different. It can be really warm in summer and really cold in winter. We're used to anything from -40 C to +40 C. Those extremes are the worst days in winter and summer though, and often in winter it will go between -15 and -30. There are nicer years and worse years. In places closer to the coasts like BC or far east it is generally warmer in winter.
Taxes in Canadian provinces:
http://en.wikipedia.org/wiki/Sales_taxes_in_Canada
If you want to get a bit of an idea about job availability and what pay is being offered, go on www.jobs.gc.ca. You can search for jobs in both Regina and Winnipeg. Go to job search tools there and then job search, and after that you'll be able to choose the province that you would like to see listings for.
I haven't lived and "experienced" Regina so I can't say much about it, but hopefully someone will lol, otherwise, maybe you can keep checking on the net and find some things out.