You've got $ in the jeep, and its already at least FWD. How about a set of winter tires and enjoy it for a little longer? Depending on the model year, some of the body styles are actually really nice, practical, good vehicle. It could be worth keeping, and just as capable with winter tires.
If you sell the jeep, I would be cautious about the tahoe. when gas goes back up, you'll have less available $ for repairs and maintenance. They are stout vehicles, but they can and do still develop hard-to-trace problems when they age, ask me how I know. Plus the plastics get brittle, like the dash, and every repair ends up with more squeaks, rattles, or brokes. Depending on the year, you may find the compass having a more comfortable interior, less NVH, etc..
Or sell the jeep, avoid the tahoe, and just pick up another AWD or FWD vehicle. It's easier to drive an old car if you have another old car to swap with during repairs. Perhaps keep both?
