I only got 2/3's of the way around last month, bailing down Twin Brook, the thought of going up South Twin & finishing at a time I estimated to 19 or 20 hours after I started & then driving back to CT was too much.
By going up Osseo, bail out routes down Franconia Brook & Twin Brook are in good locations if you want to bail & it's still a 25+ or 28+ mile hike depending on which one you descend.
If you go up Bonds, Twin Brook, IMO is too early to bail on if you are really serious about the whole loop, which really only leaves Franconia Brook, after that the trails down are away from your car setting up late afternoon of evening hitch-hikes.
Up Osseo leaves you with the big ascent of South Twin late into the trip but after that the walk as far as the West Bond Spur is one of the easiest & flattest at that altitude. It's only up 300 or so feet to West Bond, 400 or so to Bond & then down & back up 201 feet to Bondcliff. The South Twin ascent from the hut is 1175 feet in .8.
Going up Lafayette after the three Bonds, South Twin & Galehead (after getting up Bond, West Bond & South Twin aren't bad, it's the descent of ST, just like descending Lafayette the other way) but you climb Garfield , then descend quite a bit on the other side. From the low point between Garfield & Lafayette, your ascent is (if I did this correctly by inversing my numbers from Memorial Day) in the neighborhood of 1700 feet., all of the sudden 1175 in .8 does not sound so bad, & the footing is better on South Twin, IMO.
Descending Bonds tired, even the ledge on Bondcliff, IMO is easier than descending Little Haystack on F-Ridge trail 24 or so miles into your day.