Unless you're in extremely good shape (or just crazy) Sentinel Peak should be done as a backpack trip. The best way to activate is to hike to Aneroid Lake along the E Fork Wallowa Lake Trail (1804) starting at the Wallowa Lake TH.
To get to the Wallowa Lake TH drive to Joseph, OR and continue South on hwy 351/Powerhouse Rd. Once near the southern end of the lake take a left to stay on Powerhouse Road and follow it to the end. Parking is free and you do not need a NW Forest Pass for this TH.
It's 6-7 miles to Aneroid Lake (and about 3,200 feet of elevation gain) , and then another 6-7 miles to the summit.
To get to the summit from Aneroid Lake continue south on the E Fork Wallowa Lake Trail (1804) and head up to Tenderfoot Pass. Make sure to head right when the trail forks at Bonney Lakes Trail. MAKE SURE YOU HAVE PLENTY OF WATER BECAUSE THERE ARE VERY FEW PLACES TO GET WATER FROM THIS POINT ON. From the top of Tenderfoot pass you will see Pete's Point (W7O/NE-003) directly west and 9100 - Dollar Peak (W7O/NE-173) directly east.
After descending Tenderfoot Pass the trail will fork again. Head right on Polaris Pass Trail (1831). THERE IS NO WATER FROM HERE TO THE SUMMIT. If it's early in the season, you may have water at the fork. You will know you're at the top of Polaris Pass when you can see almost the entire western part of the Eagle Cap wilderness, and looking down you see a steep bowl of loose rock. Instead of heading down Polaris pass, head directly south along the ridge and follow the goat trails up to the summit.
The ridge is very narrow, and has lots of loose rock. One false step and you wil fall a long way. There is not a lot of room at the summit to set up an antenna. Good to have a partner holding the mast for you if activating HF. 2m is tough unless you can get one of the local Enterprise hams to help you out and rally the troops.