Hey Tyler.
They won't let you spend the night outside the wilderness office down in the Valley. They'll boot you right out, and that leaves you with absolutely no place to legally spend the night when they do.
With the other ones, they may, they may not. Bring a chair if you do, because the moment you lay down, you're camping and violating the law. No sleeping in the car either. They check.
Still, the best way is to do it by getting there at 11am the day before and then spending the night at one of the backpacker's camps (you have both a better chance at your desired permit and a guaranteed place to camp).
Half Dome and Cloud's Rest aren't associated other than being on the same basic ridgeline and being made out of granite. Two entirely different destinations and permitting requirements (no quotas on CR). Out of the Valley, you want a Happy Isles entry with an LYV pass-thru for anywhere beyond that point, including CR. For convenience, you can go up from Happy Isles, hit CR, go to Sunrise Lakes, then back down the JMT and exit at HI too. One-way hikes always leave you with having to get to or from the car.
From the north end, you can come in through Sunrise trailhead, or you can go up to Tuolumne Meadows and do the section of the JMT beginning at Cathedral Lakes, especially since you have 5 days. Also, your chances for a first-come, first-served permit go way up during weekdays, no matter where you go. And any way you do it, if your route can reasonably take you past it, you can attach the HD permit to that wilderness permit, if it's available.
I'll call it like I see it; Tunnel View is a crappy overnight hike in and of itself. It's a bad entry point and not much more than a downhill way out when you're done with the South Rim. And anything out of Glacier Point comes with limits like minimum legal distances for camping, and in the case of the Pohono, only one place with reliable water, Bridalveil Creek. Don't get me wrong, it's worth it for the views, but it's a better day hike. If you can manage to spend 5 days doing it, you're lost, or you enjoy sitting in one place for long periods of time. At best, it's 2 days and one night.
Here's this:
https://www.nps.gov/yose/planyourvisit/ ... lheads.htm What you have to remember is, wilderness permits aren't entirely selected by a lottery, they're only 60% reserved and 40% left available by walk-up. So, in other words, taking out popularity, you have a 40% chance of getting what you want, but that day before at 11am, weekday, and overnight in a backpacker's camp the night before are all important things to remember in adding to those chances.
For you guys, with 5 days, the first choice for what you probably want to see and do should be entry at the Cathedral Lakes trailhead, a diversion over to Sunrise Lakes and CR (HD if you can get it), then exit in the Valley at Happy Isles. Either leave the car in the valley and catch the YARTS shuttle up to Tuolumne Meadows at the start or back up there from the valley when you're done. Check the YARTS schedule online (you want the Hwy 120 schedule), but they generally have two departures from the valley per day, one in the morning around 8am, and another at about 5pm.
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