bigxxx,
Got you covered like a defective electric blanket that caught on fire.
So you are going to be downtown and it would make sense to stay there (If you stay in PB its close to a $40 cab ride downtown- not really because of the distance, cabs are expensive in san diego).
That being said, you should look into staying at:
Solamar - decent boutique chain mostly based in SF
Hard Rock - San diegos version of Las Vegas and everything that comes with it. Even has a sunday pool party in summer like Vegas. Think tribal tattoos, girls with back tattoos, spiky hair and Affliction shirts. I shouldn't have to tell you this is not my steez. Even when I was 17.
Ivy (now Andaz I think) - competitor to Hard Rock, hit or miss
W Hotel - hit or miss
Manchester Grand Hyatt San Diego - corporate monster (side note: hotel with the most rooms in CA, most people don't know that little fact.)
Se Hotel - I have followed this folly close
http://www.thegmanifesto.com/2010/06/se-...ault.html, still, you might be able to swoop some fly girls there. Hit or miss
Grant Hotel - old school grand dame, although they made it worse with the renovation.
These are probably the most expensive hotels in town although one should suit your steez. They all have some merits as a spot to post up and grab a cocktail as well. Cheaper hotels I can't really help you too much although you could probably get some great deals at these as the Down Economy has all but decimated san diego.
As far as nightlife, I need to tell you I have been mostly in Beverly Hills when I have been in CA so I haven't gone out too much lately in san diego. Some of these tips may have expired.
Tuesday night- good luck with that one. San diego is a weekend town. This is the night I would just walk around. The good thing is, most bars downtown are on 4th, 5th, 6th, street so you can see what is good and step in.
Wed night - Side Bar is the historical favorite. (this may have changed) Glittery shirt spot kind of, but probably some fly girls. Girls will be pretentious, but who really cares if you are just going to swoop them. This is your typical san diego trying to be West Hollywood spot all the way down to the drink prices.
Thurs night - Sat night - lots of options. I would start with a cocktail at any of the above hotels and ask the smoothest bartender the score. A little grease never hurts.
Some low pro tips -
Daygame downtown is no Riga, Latvia, but you could check Horton Plaza, an outdoor mall. Also a day grind in Little Italy is smooth and there is a sat farmer market that has some decent girls (super low pro tip).
Maybe check Cafe Sevilla for salsa. I believe it moved recently from a spot it was in for like 20 years. Could be a good during the week move as well. Hit or miss though. It used to be across from La Puerta that can be a good Thurs move.
If you want hipster girls downtown go to El Dorado. Hit or miss. On 14th I think. You can walk there.
Searsucker restaurant - Hottest restaurant (I use that term lightly) in downtown. The spot if you want to post up at the bar, Suited Down, eat some apps and take advantage of your tailors work and brutally handsome good looks. Girls will step to you here. Sure, the girls will be retarded, semi-difficult, but pseudo classy. Again, you are not looking for your future wife, just some girl to share your alarm clock with you.
Other things to keep in mind (I think I have mentioned before):
Watch for cops
Watch for last call
Let me know if you have any more questions. Good luck! and report back amigo.