Hello High Trek,
Our team of 3 first-timers successfully summitted on Saturday May 28th (day 2 of a 3 day trip) - so here, hopefully, are a few answers to your questions.
Following the trail: It pretty much disappears into the white above about 9,500', though we found segments exposed, and certainly plenty of footprints to follow. You kind of get to pick your own route - use your best judgement. I'm sure it will only improve this week in the summer heat though. Still, there is a LOT of snow still up there, and above 10,000' that's probably all you will be walking on, all the way to Trail Crest. I'd be surprised if it changes that much between now and this coming Saturday. Crampons (early in the day) and snowshoes (after about 1pm) were both essential. An ice axe is a good idea too, for self-arrest if you have to - there are some long, pretty exposed snow slopes we found ourselves on. We did not do the switchbacks up to Trail Crest since they appeared partially obscured; we opted instead like everyone else for the couloir to the north - a long, hard slog but manageable with crampons, ice axe and a solid amount of grit and determination. The trail above Trail Crest did not require any roping up - for the most part the trail is clear, or on low-grade rocky snow slopes. The worst problem up there was post-holing up there, especially on the descent when the snow got soft. Aside from that, there are just a few short sketchy bits on the trail with pretty severe exposure, where extreme focus and some very careful footing in the snow is required. Then again, this will surely have melted still more by the weekend so might be less of an issue for you.
Boots and equipment: I took my entry-level Vasque gore-tex boots and they were fine, got a little wet especially after all the post-holing on our descent - so I'd say whatever you're most comfortable wearing is fine, as long as they're waterproof. Gaiters were essential too. We rented axes, crampons and snow shoes, and even with limited experience in their use (a snow travel class 2 weeks before) found all of them very necessary in making our progress quicker, more secure, and more enjoyable. Take sensible layers of clothing, including wind and waterproof shell (top & bottom) - the wind up high was freezing cold late in the day and at night.
One crucial point - DRINK WATER, lots of it. On someone's advice, I started hydrating 3 days before the climb, chugging down about 4 liters a day (yes, you will pee like a horse, but seriously, I'm convinced it helped me) - and then took a 3-liter camelpak on the hike which I refilled several times. Kept sipping all the way, no problem with dehydration, no headaches. Bear in mind that there are mixed theories about the safety of the water available up there, either from streams or melted snow - anyhow we chose to purify everything with iodine tabs, and so far so good. For food - Clif Bars and Trader Joes "Tasty Bites" dinners. They got us to the top - but I never want to see one of those things again. One note - if you're camping, you will need a bear canister for storing all edibles - even up at Trail Camp, where there are supposedly no bears, marmots and ground squirrels can make life interesting.
Lastly, regards your timing: I can only pass on how long it took us, as three 30-something first-timers, with little to no experience of snow travel, of fitnesses ranging from very fit regular marathon-runner to averagely healthy thrice weekly 3-mile jogger, in the current conditions on the mountain: Day 1 - departed at 6am, and including some very necessary 1/2 hour rests, it took us almost 8 hours to reach Trail Camp; Day 2 - a 7am departure from Trail Camp, 5.5 hours to summit at 12:30pm, and 4 hours to descend back to Trail Camp at 5pm; Day 3 - 3.5 hours to descend back to the Portal, by noon. It was not easy; even in 3 days, it was a tough outing with a variety of different weather, temperature and surface conditions. It did make for a really rich mountain experience though. Now, the summit is achievable in one day right now, because we met others up there doing the one-day shot - though I was certainly glad that we weren't trying it that way! Starting at 4am, I'd say you are in for a long, extremely arduous but amazingly rewarding day if you're not camping over. I would say though, that starting at 8am, your friends will not summit unless a) they're supremely fit, very experienced with snow travel, and well acclimatized to high altitudes, or b)they're planning on camping over at Trail Camp for a Day 2 summit. Bear in mind that the average round-trip time, in summer, is 16 hours - and current conditions are still pretty wintery. In any event, note that one very real danger is the possibility of late afternoon thunderstorms if you summit later in the day - both days we were up there the cumulus clouds started rolling in at about 2pm, and it seemed like a good idea not to be hiking with the possibility of rain or much worse, lightning in the area. If you can summit before 2pm, so much the better. One guy came down the same evening we got to Trail Camp at about 7:30pm after his 4pm solo summit, and described the experience of being up there that late, that close to a possible thunderstorm, as VERY scary. Added to that, you absolutely don't want to be descending in the dark. So I'd say plan your timing around that - above all things, a basic montaineering rule I've heard many times, agree on a time to turn around and descend, regardless of whether or not you make it to the summit, and STICK to it without exception. No prizes for getting stuck up there overnight without shelter!
Whatever your plans though, go with the attitude that it will be a wonderful trip even if you don't get to the top. This is a beautiful, unique and spectacular place that very few people get to see in the state it's currently in - you will not regret it, regardless of how far you get.
Hope all this answers your questions! Feel free to fire away with more, though there are many out there with way more experience than us, (who should PLEASE correct me where I'm wrong or where their experience differs) I'll try to answer as best I can, with the experience we gained over a truly incredible, memorable and thrilling Memorial Day weekend. Two main things I learned - 1), this is a BIG mountain, and don't underestimate it - and 2), by the same token, don't underestimate yourself, because with careful planning, a little knowledge, the right gear, the right attitude, and some common sense, you can do it! Thanks to the folks at Sierra Mountaineering in Bishop for their tips and teaching on the finer points of snow travel, to all te posters on this board for their sgared knowledge and expereince, to all the great people we met on the mountain doing the same thing we were for their shared experience and companionship, and to my super-human super-star teammates Rich and Stu for making it such a blast.
Kilimanjaro's next!