If that was the year at Anime Boston that they used the alcoves and he was put into one, that may have been the main issue with why he did poorly with sales. The alcoves were often overlooked or people just didn't know they were there and therefore the profits were poor to none. Now at AB we have the third floor ballrooms, all open and more than enough room.
This will be our first year to Portcon but so far it seems better than Another Anime Con, in which we gotta share the Artist Alley room with the Dealer's Room :\ So it'll probably be a good size crowd but not packed painfully.
That being said, it may depend on what he's selling, if his art has improved at all since he last tried, and most importantly, the table itself.
If he just has a binder open with prints and a few business cards, that's no good. There are plenty of places to check out online where you can get some good tips for spiffing up your table. Anime Boston's site even has a short comic that shows and tells what one can do.
Also what he may wish to consider is to do on-site commissions. Go as cheap as possible and have a cap on how many you think you can do at once (otherwise you could be swamped and not be able to finish everything on time). Though for that kind of thing, be sure to have some kind of internet access because fanart is the biggest seller.
Personally, I don't care for the majorty of what's in his gallery and the style just isn't my thing, but he should give it another try nonetheless C: Good luck to you both, see you at PC!