Bartender played hooky?
 

For testing purposes, I converted the Roller Rink lot to an all purpose lot -- added dining, coffee, and bar. The barista, cook, waitress, and maitre d' appeared on the lot when my Sim arrived, but no bartender! There doesn't seem to be a bartender in the NPCs either.

Is there a trick to putting the bar together so a bartender will come?

The bartender is showing up for me in Crypto's. That uses the green dayglo/neon bar. I don't think you can use the ordinary TS2 bars, I think they have to be Uni or NL and greater. Are you sure it's possible to get behind the bar?

MikeD

Yep, there's a free square all around it except where the island is. What catagory are the bars in?

Try looking in Misc -> Party

I think you have to go over $1000 to get a bartender. Of course you could always hire a DMA bartender.

MikeD

Lol, this is your basic unowned Community Lot. I got it working and got a bartender.

I just added a Shopping District and a 3-in-1 Bookstore. The bookstore added the bartender and a clerk as well as one additional Townie.

So it looks like any visit to a base 'hood or OFB Community Lot gets you one Townie and any visit to a Downtown Community Lot gets you a Downtownie, plus sufficient NPCs to run the lot.

I'm about to add a University and count those new Sims...

The next run added: a cafeteria worker, 4 Dormies, 24 Professors, and a streaker!