Flagtail mountain is not close to any population center. You can get to it from John Day by traveling south on US-397 and then turning west onto Izee Paulina Lane. Travel this paved road to 44.1618, -119.2511 and turn onto a good gravel road. Drive ~5 miles to an active lookout.
Mount Baldy summit has a Forest Service Lookout tower and a multi-agency communication site for the NW corner of Montana. There are good views from the summit including high mountains of the Cabinets Mountains to the south, the Selkirk Mountains to the west and into Canada to the North.
An easy summit in the John Day area is Long Creek Mountain. To access it turn east off of Highway 395 on NF-3940. This turn is at the Long Creek Summit, 44.6789, -119.1309. The turn off the highway is steep, but I believe it is Priusable to 44.6626, -119.0480. From here it is half a mile and 250 ft. of gain on a rough road to the summit. You can drive it with high clearance and your mirrors folded in, if you don’t mind a few paint scratches.
Summary - Lookout is drive up with a wide open summit, though parts of the way up aren't for the faint of heart. There is a small comm facility that doesn't generate appreciable RFI, a couple of places to set up, and when the clouds aren't in the way, excellent views. Bring a mast if you want to put up a wire. 2M contacts are possible with a 1/2 wave whip but a yagi will make things a lot easier. APRS is easy from here, too. Drive time from SE Portland is about two hours through Stabler and out Hemlock Road (turn at 45.80838, -121.90741).
Cuddy Mountain, W7I/SR-055, is ALMOST a drive up summit, if your vehicle can handle it. The road to Cuddy and Summers requires careful driving, high clearance, and 4WD certainly helps. I was glad we gave an extra day for the snow to melt out because there were a couple spots that would've been more difficult to get through in the Explorer if it had been deeper. A couple mud pits looked suspect, but be made it through okay. The roads up here are frequented by off road enthusists and you'll likely see some UTVs, ATVs, and dirt bikers.
Blind Cabin Ridge is a 1 pointer with few activations as of this writing. Access via Barney Reservoir may be gated, so check ahead of time. Thank you to Ryan W7RMR for his write up on the PacNW SOTA facebook group.
Lookout Mountain is a US Forest Service active Lookout. Though not has high as some surrounding summits, it is typical of lookouts having good forest views. The summit is accessible by automobile. Trees are available for hanging wire antennas. &