Based on your description you dont have a lot of great options. No matter which way you go, you are in for a lot of rock hopping. I dont think I have hiked with you so I can only make recomendations based on what you reported.
The best option is an overnight at Chimney Pond but getting reservations is going to be tough unless you dont mind late season hiking. Looking at the reservations (as of today) starting on 9/17 to the end of the month it looks like there are bunkhouse spots. Not a lot of privacy but the bunkhouse has a woodstove which is real nice in later September at Chimney pond as the sun sets early and the temp drops quickly. The great thing with Chimney Pond is you can start late and get back early as you have no approach to deal with.
From Chimney Pond, the easiest route is up Saddle to the tablelands then an up and down to Baxter Peak and then an up and down to Hamlin then back down saddle. Note Saddle is a slide with loose gravel at the top and boulders on the bottom but overall its the easiest of the approaches. If you are feeling good on Hamlin, I highly recommend going down Hamlin ridge trail, its a bit more work than Saddle but the views to either side are spectacular, plus you can look over at the Knifes edge. If you were staying at Chimney Pond, the hike would be 6 hours round trip as a swag. Going up Halim ridge is also a nice hike but I figure the best option is to head up Saddle and bag Baxter Peak then assess how you are feeling and either skip Hamlin, do the out and back or take the ridge down.
Even if you arent staying at Chimney pond, Chimney Pond trail and Saddle it is the best option for a day hike. The hike from Roaring Brook to Chimney is an old logging road, bony in places but fairly easy going.
I can not recommend Abol or Hunt Trail (AT) from the west, the distances may be short but they are steep, you may not have issues going up but it would be hard going down as there is a lot of jumping or sliding down over boulders. Of the two, Hunt Trail has the best footbed with no real loose slides but the hike up through the boulder field is quite strenuous with lots of upclimbs over boulders. By the way the views are spectacular as the ridge is only 40 or 50 feet wide in some spots. The boulder section is about 1/2 mile long but the rest of the Hunt trail is real well built and easy hiking.
I havent been up Abol for many years but my memory of it is similiar to the south slide on Tripyramid, lots of loose rocks and gravel in spots. Both trails join up on the tablelands, the tablelands are impressive but some find its a bit intimidating as it feels you still have a long walk to the summit once you clear the headwalls.
I also dont recomend Dudley unless you like boulder scrambling, its about as steep as a trail can get going down and even someone with good joints may ache for a few days.
A general note is that water is scarse up high on the mountain. Its easy to run out Thoreau Spring can be a mud pit. Saddle Spring is usually running but I would still treat it.
I will be up there Labor day weekend.
