You might want to hold on to the REI tent for your Shasta/Rainier trips, as UL tents aren’t really designed for above treeline conditions.
If you do decide to trade in your tent, you could stick with REI. Check out the review of the Quarter Dome T2
But really, tarptents are totally the way to go for someone who wants to lighten up but isn’t ready for a tarp/bivy. The Scarp 1 and 2 are double walled like a conventional tent and along with the Moment and Rainbow could likely handle moderate below treeline winter conditions.
As far as a sleeping bag, i’s just about impossible to get around owning at least two if you want to camp in both summer and winter conditions. The closest you might be able to come is to get a full zip 20 degree bag(or quilt) that you can unzip and quilt in the warmer temps, and use the insulation you’re bring along on colder trips(down jacket and insulated pants, using your shell jacket/pants as a vapor barrier) to bring the temp rating of the 20 degree bag down to 10 degrees +/- how much insulation you are wearing. Myself, even quilted, I couldn’t stretch a 20 degree bag past 35-40. I’d just get too hot. So it’s 2 quilts for me.
The thing about two bags is that you can combine them. Get a 40 degree synthetic(or down)bag for summer. Get a 15-20 degree bag for winter. Sized appropriately, you could layer the two bags to take you close to zero. (Again, combined with the insulated clothing you’d be bringing anyways)
If you really like the Thermarest, consider going with the shorter 47″ length and saving 9-10oz. Do you sleep on your back or side? I use a 47″ Neoair and sleep on my side/stomach. At 5’10”, the NeoAir pads me from my head to my knees. Use clothes or your pack under your legs.

