The reason that Timberline operates all summer long is due to the Palmer Glacier. It is really more of a permannet snow field or crevasse-less glacier. by late July, there is no snow left at lodge level (although this year there may be) and you carry your board in hand and ride up the magic mile lift to the base of Palmer, then strap in like normal and get on the Palmer chair which takes you to the top of Palmer. It is about a mile long and about that in width in places. The entire thing averages about 30 degree pitch and they build race lanes which are closed to the public untill around 11:00 AM then the entire thing is fair game. They always build a decent series of terrain parks on the glacier as well. This is in addition to the area set aside for the camps. In May, you will have Palmer and all of Magic Mile available and possibly some of the lower runs if the snow stays good and they decide to run the chairs.
Weather will likely be warm and sunny, but it is Oregon and at the elevation you can have a white out blizzard even in July. In fact, every month of the year, they get at least a trace of snow. Plan on riding warm but make sure you bring gear to deal with winter like conditions. Also, if you have 2 sets of goggles; one for bright glaring sun and one for low light/night, bring both because the fog can reduce your vis and can happen anytime depending on regional weather patterns.
Sandy is 30 miles from Government Camp and the Tline road is about 7 miles up to the top. Road conditions should never be in question by this time of year, so a plain jane economy 2wd rental car is more than adequate that time of year.
In Portland, there is everything from an abundance of night clubs that favor everything from Punk to to country /western Great theatres, there is the OMSI/Imax, great parks, skate parks and trails. Clackamas Town Center has a huge mall with dining, shopping and movie theatres. For outdoor recreation, Mt. St Helens National Monument is about an hour up I-5, Multnomah Falls is just up I-84 at exit 30. It has amazing hiking trails and breathe taking waterfalls. The entire Columbia Gorge is a a great scenic drive. You could take a day and Drive up I-84 past Multnomah Falls to Hood River, cross over to the Washington side of the Columbia, and drive the 20 miles to Trout Lake at the base of Mt. Adams then come back to Portland vie WA SR 14 along the Columbia river on the Washington side. On that route there is Beacon Rock State Park with awesome hiking trails to amazing viewpoints.
Hell, if you want to help me out with gas, I can drive you around this loop and we can hike a few of the better trails..just let me know.
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