Jeff,
I currently do a 22 mile one-way commute in the Minneapolis-St Paul area on an ODK U500 with a 32ah battery - I have not done it year-round yet so I can't comment on the winter riding aspect, but I plan on getting some studded tires and giving it a go this winter. I'm not sure how many other winter e-bikers there are on the forum - hopefully they can chime in. A few things to note that I've learned:
1. If those passes are unlimited ride passes, then I don't think you'd have as much benefit as you probably will not want to give them up as doing 48 miles (assuming you're talking about 24-mile one-way) 5 times a week can become a bit exhausting, even if a motor is doing most of the work. That's my perspective at least - I find 3 times/wk on bike and 2 by car to be my happy medium, especially since I have things I have to take care of occasionally after work. Also, if there's a wicked storm coming your way, it's always good to have another option to go to - sounds like you could do the one-time passes instead of the monthly in this case.
2. Another consideration is time - for this reason I think getting a speed pedelec is a good idea so you can hit 28 mph and cut down on your round trip time. My round trip for the 44 miles is 2.5 hours - this adds up to 12.5 hrs/wk, 50 hrs/mo. This is about 5 hrs/wk and 20hrs/mo longer than if I drove, so that's lost income for an hourly job assuming you'd have worked those hours, and that has a cost that may be worth factoring in.
3. What would your route be? Are there good trails or bike lanes that can take you all the way?
4. Night riding will likely be in your future so you'd have to outfit yourself with lights/reflective gear galore as well as some extra cycling clothing - that stuff also has a cost although it's pretty minimal in the grand scheme of things.
5. Getting a battery as ginormous as the 48V32ah one I have is likely not needed - I can do my round trip commute on one charge - if you have a smaller battery just make sure you're not cutting it too close.
6. If you're going to be on shared trails, be aware of the laws as well as your motor noise. My motor is a bit louder than I'd like personally for shared trails - I kind of wish I had gone with a BionX D500 setup (Ohm U700 for example) since it's super quiet and can get up to 28 mph. Only downside is a smaller battery so 24 miles one-way might be a slight stretch.
7. The $2000 price point may be hard, just because you'll need good a larger battery and good components. I would go for something more around $4,000 - the payoff period will be longer but you'll likely get a more reliable product. Going cheap I think is a risky bid since if parts all begin to fail in the first few years you'll end up paying more in the long run if you have to buy another bike in two years.
Just my thoughts for now - good luck on your search!