Peakbagr has a good comparison for Chocorua. As I also speak the two fluently.... Garfield, 10 RT, never really steep, same with Osceola which is about 6.4 RT unless you up from Greeley Ponds, then it is steep.
I'd say the Osceola comparisons are either Hurricane or Wrights's Peak. Both are bare offering extensive views, one s almost 3700 feet, the other 4,580. Giant is not a bad choice, it is a pretty steep climb with places with views when you need a break. If Monroe stood by itself, the trip up the Ammo would be similar to Giant IMO.
For a Garfield comparison, I'd go with either Phelps or Colden Phelps is shorter, but is easy for much of it and then a decent climb in the last mile, harder than anything on Garfield and a bit eroded. Colden by Lake Arnold is more than 10, very easy to the old Marcy Dam, then as you get closer to Lake Arnold it is a bit harder. The last bit on the Lake Arnold Trail is pretty steep, however, once you get out of the trees, it's a great view and not to long. (The Trap Dike is their Huntington Ravine or Six Husbands, maybe even harder, don't go that way.)
Cascade and Porter are often done first, they have a high crowded start from 73 and the saddle between them is pretty easy. Steeper than Osceola, it's not too bad, they probably compare with Osceola, I'd try to do Cascade & Porter mid-week if possible. Regarding the WMG Vs the High Peaks Guide, I would say that when the ADK guide says steep, they mean really steep. The Three Agonies on Lafayette would not be so nicknamed in the ADK & the South Twin climb from Galehead would be Moderate to steep. There is terrain similar to Flume Slide or the Tripyramids, but no headwall trails.
Parking is an issue in the ADK. Hurricane is on the road and likely less crowded than any other listed. Colden, Phelps & Wrights is all done at the High Peaks Visitor Center at the ADK Loj and parking is limited and roadside is not allowed so weekday or an early arrival is a good idea. There are a couple of hostels or B&B options in the area if staying up there the night before tp save yourself from a 4:00 AM start (which may not get you into the Loj lot depending on what you call Central MA.)