When will he be there? and will he be solo all the time?
If he has any reservations about the hobby hook him up with POPS. POPS runs a wingman service and it is a great deal for Newbies. Your friend will not be alone and will get a good introduction to San Jose. Web site
www.popsguideservice.net
As he will be there solo and it is his first trip, Sportsmans is the best bet. Great selection of ladies with out the attitude of the DR ladies. The courtyard rooms are good and a little less than the new wing. The Mansion is usually booked; I do not like the club house wing.
Plenty of advice at the bar all the time at SL and plenty of potential wingmen.
You may want to try Hotel Little Havana. Ladies are regularly available and it is part of the MP. Room service is available. The bar is a good place to find wingmen.
If you can not get him into any of the usual places try the Sleep Inn. Easy walk to DR; just around corner, and a short walk to SL. It is convenient for most of the MPS. Biggest issue is the $25.00 chica fee, it may have gone up, and it is not exactly chica friendly but they do tolerate it.
Check out the Hotel, Resorts and Accommodation section for other reviews.
I also recommend PM'ng POPS or other members before the finalizing of the dates of the visit, check out the Roll call section and see who will be there. They may be able to arrange a meet and greet for him, or just ask in the this section.