1. First thought is why not start out Saturday or Sunday since its a weekend anyways? If nothing else I probably will just because I will be sitting around, especially Sunday. My other thought is 2 days is way too much drive time. Admittedly one day is a tough drive, and I am not a fan of that these days, but you could do 10-12hrs one day, half a day the next and get there early enough to wheel and not be trashed. Otherwise maybe a warm up trail on the way up the Eastern slope? See 3.
2. I would start with Barrett Lake, its before the Con.
3. To break up the trip home I would suggest a Eastern slope trail further south, lots of options, mostly Easy to Moderate but scenic. Always wanted to try that but never have. Start out early home the last day and it will be a cake drive.