You can look at the icons on your Servant/Prisoner list & even mouse over them to get further details on that icon, it's not necessary to click into every individual character to check their details. I get that some of the icons may looks similar (like Plague & Dirty), so mousing over helps if in question.
The game also gives you alerts if one of your characters contract a disease (it literally stops the game until you click on the confirmation button), so it's not impossible to take care of when it happens. You could also do what I do & use screenshot software to take notes of what you need to take care of or add them to some form text document on your PC (or in the worst cases, write it down on paper) before dismissing the alert so you can come back to it. I've also been keeping notes in the names since it don't cost anything to rename the characters in your dungeon (makes it easier to keep track of their relationship status towards you when certain random events hit & tailor your decisions when the options are given).
You could also use the codex function in the game to go to a specific status (or ailment in this case) & it will tell you what characters have that status on them (screenshots can come in handy here also, rather than having to go back to the codex to find a link to them again).
As for new characters that are either joined or captured, I make it a point to always check the stats on them the first time I run into them; this can come in handy in determining if you even want to keep them & are willing to just sell them over the market (or when a slave trader visits your dungeon, provided they request one you don't want). They are always sorted in the order of when they were generated in your dungeon, so new ones will always be at the bottom of that section. The exception is that if a character is recently converted from a prisoner to a servant, they will still be sorted by the order they were generated, but they won't be sorted by the time they were converted as a servant (this means if more characters are generated since the time you captured a prisoner, they prisoner won't be at the bottom of your servant list).
As for auto-dressing if clothes are available, I'd say this needs to be a togglable option if it does get added, so the player can decide whether they want to use it or not. There are certain clothes I don't like on male characters, I'd rather chose what they are wearing rather than having them throw something feminine on...
EDIT: Something I forgot to mention: Do a search for Gadwin PrintScreen online, this is the same screenshot software I use.