I skied Jiminy in High School. It did ski pretty big considering its vertical and yes, the Timberline analogy definitely applied back then.
However, it appears that Jiminy has made some big changes as of late:
http://skitown.com/resortguide/stats.cfm/ma11/JiminyPeakBase Elevation: 1,250 ft (381 m)
Summit Elevation: 2,380 ft (725 m)
Vertical Drop: 1,150 ft (351 m)
Skiable Area: 170 acres (69 hectares)
Annual Snowfall: 100 in (254 cm)
Snowmaking: 93 %
Number of Lifts: 8
Uphill Lift Capacity: 12,800 per hour
Types of Lifts: 1 Surface Lifts
1 Double Chair
3 Triple Chair
2 Quad Chair
1 High Speed Six
Number of Trails: 43
Longest Run: 10,560 ft (3,219 m)
From looking at the trail map, it appears that many trails cover 1500 of vert, which is a good thing. The snowfall number is less than WV, which is not good, especially if snowmaking is lackluster. However, the lift situation looks good. If it were me, I'd take a chance and go and if things are bad snow-wise, day-trip it to Stratton or Mt Snow.