Summary - From Portland, a long, relatively easy drive (2WD okay) and a short, difficult bushwhack will net you a big beautiful view from a very small summit. 2M is likely to be difficult, bring a mast if you want to do HF, and be prepared to scramble if you want to operate from the summit itself.
Summary - Steamboat is an easy (if longish) drive from Portland, reached by a short climb along a lovely trail, and has terrific views of all your favorite volcanoes. There are trees for antennas and plenty of places along the ridge to sit and enjoy the view. VHF is relatively easy when using a decent antenna.
Summary - This Haystack Butte is easy to get to, if you don't mind the possibility of new pinstripes (and it is not the MC-070 peak). The bushwhack is about a quarter-mile, not steep, and mostly requires negotiating large deadfall. The summit is broad, flat, tree-covered and doesn't have much of a view. VHF contacts are likely to be difficult.
UPDATE - K7AHR decided to check the ground conditions for these two peaks. Both are apparently accessible with the usual cautions regarding hiking in burn zones.
Hearing that the Big Hollow TH is again open, I began making plans to activate Timbered Peak and Sister Rocks (W7W/LC-064). Unfortunately, a BARC map (dated September 30, 2020) indicates that Timbered Peak was severely damaged in the Big Hollow fire. At this time, there appears to be no way to safely access either summit. More below...
Summary - Northwest of Trout Lake, WA, Flattop Mountain is the site of a microwave tower and a couple of repeaters. While it is a driveup, the last section of road is best negotiated in a 4WD vehicle with good tires. There are no views and little open space on the tree covered summit. As with other hills in this area, ATT cellular and APRS coverage are both very good while making 2M contacts is hard. Flattop is not on my peaks-I-must-visit-againlist, though I would probably include it in a multiple day peak excursion.
Summary - Peterson Ridge is a relatively easy bushwhack and an unremarkable summit, without a view or open space. The pleasant hike in on Service Trail 35 includes a modest climb and is mostly under the trees. There are trees for antennas, ATT cell service was five bars, and two way APRS messaging worked. I had no luck on 2M, even with a yagi. The drive can be done in a passenger vehicle and there is plenty of parking at the trailhead. One caution: This is a busy part of the forest and this trail is frequently used by motorbikers.
Summary - Little Huckleberry's small summit is open, has terrific views of the surrounding mountains, and is a nice place to operate. The trail is easy to follow, climbs about 1800 feet over two and half miles, and is popular, so an early start is a good idea. Bring a mast if you want to hang a wire. Two meters works okay. Both APRS and ATT digital service are reliable.
Summary - Roughly two hours from Portland, getting Mann Butte includes a steep bushwhack through heavy brush and deadfall and ends in a small, tree and brush covered summit. You can see Mt Adams through the trees but not much else. While you can drive to the base of the summit, if you value your vehicle's paint, you will hike the road in.
Summary - the hike to 3977 (from copper creek) is relentlessly steep, easy to follow and ends in a summit with great views. The route on FR 41 from the Sunset Falls campground is festooned with holes and washouts, some of which are spectacularly large.
Summary - Given the two hour drive, a really steep, brush covered cross county hike to the summit, and the need to bring HF along, summiting 4220 is best part of a multi-hill day. A map and compass or GPS is a really good idea, as are trekking poles and long pants.