I live in CO too and the commute in and out of the mountains is not going to get easier. Personally I like enough get up and go to pass anybody I need to safely. With that in mind I like a simple dependable SBC (mine SBC 400) that 'you' can work on. Injection is nice but I have no issues with a 600CFM Edelbrock either. You'll probably need to add a little weight seasonally if you want traction in the snow. So many variables, let us know where your headed.
I would go with a common v8. The ford, chevy, and chrysler small blocks have stood the test of time and you aren't going to have any trouble finding parts for any of them. If you are more interested in an inliner, the same as above applies. And while I don't know much about the slant six, ford's 300 and chevy's 292 both make good power and are pretty durable.
Chevy 350, 383 or 400. Very common. Easy to produce bolt on power. And INEXPENSIVE to fix. If its a driver, ford and mopar parts can cost you 2 to 3 times a Chevy part. Maybe a cookie cutter but when it comes to reliability and cost efficient parts... Can't and won't go wrong with the 350-400 My $.02
The best and most durable modern inliner out there is a Ford 300" six. Get a later one with fuel injection and a 5 -speed or overdrive automatic and you'll have a great combination that is as reliable as an anvil. Incidentally these engines come with "split" ext manifolds from the factory so you can build in a great sounding exhaust system. A great engine for any inline six engine bay.
For what you're planning, I would go for a modern motor that parts are going to be readily available for in 10 years. Reality means that probably eliminates most inline 6 cylinder motors. Your Chevy is going to be fairly light, a modern V6 and overdrive transmission would be good choices. Once you choose your motor and trans, the rest will fall into place. The fact is, most drive trains more modern then the late 50s, once properly set up and properly maintained, will last over 100,000 miles. Upgrade the brakes and suspension to modern day standards, HAMB friendly or not. If you are really planning on driving in all weather conditions, time spent insulating, sound deadening, and making the car water tight would be well spent. Modern heat, defrost, and air conditioning (or a good source of fresh air) and functioning wiper system would also be a must. I have put a load of miles on some of my hot rods through the years, nothing takes away from driving enjoyment more then fogged windshield, cold wind drafts, and water dripping on you in a rain/snow storm. Also spend some time getting the seat, passenger restraint system, and steering column correct for you. If its comfortable to drive, the miles add up quickly. Gene