Summary - Termination Point, near Old Man Pass Sno Park (west of Indian Heaven Wilderness) is an easy drive from Portland by way of Carson. If you don't want much of a hike, you can drive up most of the way after turning from NF31. Just stop along the way wherever you decide that the giant mudholes or the sound of paint being scratched is more than you can bear. The final summit hike is very steep (trekking poles are a good idea) if short.  ATT cell service is servicable, APRS is good, two meter contacts unlikely.

Summary - Crazy Hills, along with Lone Butte, is on the western boundary of Indian Heaven Wilderness, near the Lone Butte Sno Park. The drive is mostly on paved roads by way of Carson (Wind River and Meadow Creek) and includes a 1.5 mi hike (mostly cross country). Drive time from Portland is about ninety minutes. The summit hike follows a ridge and requires a short steep climb to the high point.  APRS is good, ATT cell is servicable, two meter contacts are a struggle.

A near drive-up summit in the Coast Range. From Highway 36 around Milepost 20, take  BLM 17-8-31 Road, (Near 44.11999,-123.64626 and 17445 Oregon 36, Deadwood, Oregon).

Travel 4.2 miles on this Priusable gravel road and park when 0.2 miles from summit and walk up the road shown in the first photo. At the summit are remains of a fire lookout (see photos):
https://oregonlookouts.weebly.com/windy-peak.html

A near drive-up summit in the Coast Range. From Highway 36 near Milepost 18, take paved Nelson Mountain Road east. When the pavement ends just before 3 miles, turn uphill to stay on Nelson Mountain Road (my GPS called it Chickahominy). Do not go through the yellow gate - that's the 17-8-14 Road. Continue up to just past the 4 mile sign at a four way intersection turn right onto Walker Point Road.

Medicine Point is a popular US Forest Service rental lookout.  The hike is pleasant on a well-maintained good-grade trail, FS #181.  I set up SOTA operation a couple of hundred feet away from the lookout to not disturb a young couple that had rented it. Much of the southerly ridge from the trail junction to the lookout is within the activation zone.

There are several trip reports available for Rock Peak, WA. I used: https://www.summitpost.org/rock-peak/709367 which had correct directions.  It is also accurate about the hike up being a short, steep, slippery ascent with medium density forest floor brush. Peakbagger has several other reports (https://www.peakbagger.com/peak.aspx?pid=16430)

This unnamed summit is a bald rocky grassland overlooking a large mostly roadless area (Allan Mountain 01946) and the southern end of the Selway-Bitterroot Wilderness Area. It has a very good trail, FS #178 due in part to regular trail maintenance through a huge amount of fire-killed fallen trees. The hike also travels through large southerly-aspect grassland-slopes that could be quite warm during mid-day summer months.

Saddle Mountain is near the Lost Trail Pass Ski Area. The SOTA summit access road serves the upper facilities of the ski area. A high clearance vehicle can drive to within 0.25 miles of the summit. The summit has good views. It is very open and rocky with limited space for long wire antennas. 

Anderson Mountain is a drive-up for most vehicles (possibly excluding low clearance vehicles). Nearby places to visit include the Big Hole National Battlefield. The Battlefield is the site of an 1877 tragic and deadly encounter between the Nez Perce Tribe and the US Military. The Battlefield Visitor Center is located approximately 17 miles east on Highway #43 from Lost Trail Pass, Idaho/Montana border.

4.9 miles, +2,632 ft, -124 ft; Nice Hike

Driving Directions from Ovando, MT