Do you need the special shorts? Definitely yes.
Is it really bad to use underwear? I digress.
I have tested several combinations of clothing, several grades of saddle cushioning and quality (low to mid-range) and even gel covers. I came across the "no underwear" advice far too long after I started riding, so I used underwear all the time and never ever had a problem with it. However, I use briefs rather than boxers.
The best combination I've found is a good quality bike short on a medium range saddle. The amount of cushioning I use is very little for when I'm in top shape and my muscles are well tonified. A little bit more cushion for MTB or when I'm out of shape.
(Gel covers are virtually useless, I only mention them because I have used then a fair amount. I'd only recommend them for very short commutes while using regular clothes on a saddle with no cushion or very little cushion. For any serious riding, get rid of the cover)
I'm primarily an MTB rider with some experience in Downhill. I'm no road rider but I have done several road trips on a hybrid, no suspension bike.
My longest continuous time on the saddle was about 8 hours on MTB (dual susp, low cushion saddle). Was using regular bike shorts with underwear and a baggy short on top.
My road trips have been 6 contiguous days, with max 120km (about 75 mi.) per stage. Did them with bike shorts and bike shorts with tights over them. The only day I used a baggy short I had trouble with rain, as when the short was soaked, It caused stiction against my legs, adding too much effort to pedaling.
These stages where about 4 hours of pedaling, but due to the logistics of the trip I usually had to remain on cycling clothes for another 4 hours before I could take a shower, however, never had trouble with all the layers I use.
Regarding other clothing layers: I have used a lot of extra layers for many purposes.
On top of bike shorts I often use "baggy" shorts for MTB, for protection, for the looks and for the pockets.
For DH riding, I use a thing (I don't know the name) that has a lot of padding around the hips and other parts where the usual bike short doesn't. It also does not have the regular padding so it's not redundant with the bike short. On top of that I use a DH pant or short.
For cold weather, I have had success using a runner's tights specially for the thermal characteristics of it. Protects from cold, does not overheat when ambient temp rises, kind of balances temperature among different parts of the leg. (I know there are full leg bike tights, but I've been unable to find ones not made of lycra. I have a pair of lycra ones, and they are ok for protection against sunburn, but no use against cold air.)
For commuting I often use the bike short under the regular pants. No trouble at all.
I have never used chamois butter, and almost never had chafing problems. The only times I had mild cases, where precisely while using gel covers rides longer than 2 hours, or when I borrowed a bike with a saddle too wide and too padded.
That being said, I'd never attempt a long ride using a bike, or a saddle type or a clothing combination I have never tried before. On the road trips I mention, I had some novice partners having all kind of small trouble, some of them due to clothing and many due to thinking "more padding is better", poor bike fit and relying gel covers or similar things.
In their case, they had never been on their bike for long enough to notice the fit problems.
Have you ever ridden for as long as your planned trip longest stage? On the same bike or similar one? With the same type of saddle/handlebar/grips or bar tape?