I assume 'Underwear' is just an extra layer of clothing, which currently falls under the 'Dress' category (i.e. Designer Lingerie, Lace Lingerie, Leather Lingerie, Organic Lingerie, etc.).
Assuming the categories aren't mutually exclusive, I suppose this means you could put a girl in both a Royal Gown AND Designer Lingerie, meaning she'd get the bonuses from both items. In the old situation, you would have to choose whether you gave a girl the Royal Gown, OR the Designer Lingerie. Therefore, the extra category makes it easier to build stats on your girls (as you have an extra item slot to put items in which raise stats... in my example, the Charisma of a girl would be boosted by +39). To balance this out, I suppose you could tone down the stats that 'Dress' and 'Underwear' items add, to the point where a Dress + Underwear item in the new settings would give roughly the same maximum benefit as a single item before (special items notwithstanding).
As far as pricing goes, I'm a bit torn. On the one hand, it doesn't make sense if a half-way decent dress would cost more than the average girl from the slave trader would.
On the other hand, money is already quite easy to come by... either that or the girls just aren't balanced very well, there are quite a lot of girls who can earn back the 1000-1500 gold they cost within one week, if you put them to work in the brothel. If girls were that cheap, why wouldn't brothel visitors just buy their own keep-at-home girls I wonder? Where's the real investment in buying a girl for your brothel? Anyway, I digress... my point is, making items cheap as it is now might make the game too easy in general.
You might want to wait a bit with making big changes in pricing, until we know what PP's reworked customer system will do to the economy of the game. I've been piddling a bit with the pricing myself, and came to the conclusion that girls should be a lot more expensive than they are now (think at least 5-10x more expensive). It would make girls more of a rare commodity, force players to think harder about which girls they want to buy at first and I suppose slow the pace of the game a bit, leaving more room for the roleplay-like scripts and other aspects. Of course this is just my opinion, I suppose a lot of players like being able to build out their group of girls fast and will fully respect the decisions of the developers in whichever direction they want to take the game, it's awesome either way
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The therapy and education/training items sound very interesting, would those be like consumables? In any case, a bit more variation and item tailoring to make girls more suited for specific jobs sounds awesome, I'd love to see some of those in the game.