Senior Plant Needs Help?

Hi there again.  I have just one more question.  I have been hardening off my plants for a couple of weeks here and have had a few problems along the way, mainly with my 'senior' plants.  The 4 largest of the group seem to have their leaves drop to their sides and roll up / wilt?  2 of the 4 spring back in a couple of hours, but these two have stayed the same for the last 28 hours.  I do know that they need to be transplanted asap, as they are getting root-bound by now I am sure.  They are approximately 16-18" tall, and they are Caribbean Red Habanero's.  Any help or advice is greatly appreciated.  Also here are a couple of pictures of all.  The Caribbean's are on top of my toolbox, and the one in the pail is a Moruga Scorpion.  The others, well, they vary....
 
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Forgot to add that the Caribbean Reds are in 4" square pots, for another day.  Also, the main plant/stem does not fall over at all, just stays as is in the picture.  My adults are sissies! :P
 
What have your temperatures been like? And did you harden them off / how much direct sunlight are they getting at this point? How often are you watering, and are there good drain holes in the bucket? (…. and in the cups, for that matter.)
 
Temperatures have been 60-70 on average while outdoors.  I put them out at approximately 3 pm till 10 pm.  I have been hardening them off for a couple of weeks, an hour for the first days, 2-3 hours the next couple, 4-5 for a few, and now 6-7 hours.  As for light, they are getting a broken-up/direct sunlight (through the trees without leaves).  I am bottom watering when the pots are light feeling, and the soil is dry.  And as for drain holes, all of the cups have 6 drain holes approximately 5/16" round in the bottom, 5 1/2" holes in the bottom of the bucket.  Thank you for helping.
I feel a song coming on....  There's a hole in the bucket dear pepper, dear pepper, there's a hole in the bucket dear pepper, a hole! :dance:
 
Hmm…. kind of puzzling. I would be concerned about a soil fungus, but you stated they perk back up (at least some of them.) Typically they would not perk up if a fungus was getting to them. The moruga scorpion in the pail - how long has it been since you put it in the pail?  And have you repotted the others yet? Usually that kind of drooping is caused by colder temps than you have been having, when cold is the issue, but if it was the plants would perk up when it warms up. But you do say "on average" - what has your lowest low been about the time they started drooping? 
 
It may simply be that those tiny pots aren't holding enough water for the individual plant's needs, so potting up may be all that's needed. Some varieties seem to just be thirstier than others.
 
You answered your own question regarding the Caribbean Habs on the tool box.  Those pots are a joke for plants that size.  It doesn't look like the pots are even full with soil.  I have no clue about the other one.
 
How come the plants don't get sun until 3PM?  You must have a really late sunset?
 
Honestly,  they look thirsty.  Usually hot/cold temps will cause them to droop as well as being underwatered,  but those pots are really tiny for pepper plants that size.  I'll agree with geeme,  pot em up and give them a nice deep watering from the top.  Usually bottom water is geared more towards indoor grows to control fungus gnats.  Don't be afraid to soak them things down either until you see water coming out the bottom.  It's good to push oxygen through the soil and watering from the top does that.  
 
@geeme
The Scorpion in the pail was a day or two.  The others were all in the cups seen in the pictures.  As for the temperatures, the absolute low was 50 at night in the garage where they slept, just in case of frost.  They all go outside around 3 pm, and then the temperatures were anywhere from 60 - 70 degrees when the leaves all started drooping.  As for potting up, they are now potted up, in their new home.  Thank you.
 
@Roguejim
They go outside at 3 pm when I arrive home from work.  The nights in the past few days were unpredictable, so they came back inside at around 10 pm.  I did not put them out early when I leave for work as I wanted to be around in case something like this happened, so I was able to bring them back inside.  Actually, the view they all get during the hardening off process is very good in my opinion (as a first year grower from my standpoint), although I may be incorrect.  The place that all of this happened, my deck for hardening off, they get full sun till about 9 pm if not cloudy.  Now they see the sunlight directly till about 7 pm, then they get a beautiful shaded view from their new homes.  I had just found it weird as the smaller plants were all very good, with only 2 doing the same as my 4 larger plants.  Thank you.
 
@Jamison
Thank you as well for your help and input.  A good watering they will get tomorrow morning, as they got a little watering today as I was afraid to overwater.  Oxygen they will get!
 
Yes - once my plants go outside I completely soak them from the top until the water runs freely out the drainholes. We have enough wind that the surface of the soil dries out fairly quickly. I also use the lift method between waterings to see if a given plant needs water yet. 
 
Ok.  So my Caribbeans have not yet changed, but I am still giving them a chance.  As well, my Scorpion had dropped it lowest leaves today I noticed.  Here are the updated pics from this evening.  The green pail is housing my Reaper plant as well.  It was just transplanted this evening for the picture.
 
Caribbean Reds
 
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Scorpion and Reaper
 
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