I haven't read everything in this thread, so if I repeat... sorry.
Can't speak for hotel prices. Before I moved here, my company paid the bills. I have never stayed in a local hotel on my own. I would think, however, that $33 a night is quite a steal.
I will focus on food and entertainment:
- any place in Mt Adams. lots of bars and restaurants, all within walking distance of each other. also Eden Park with the art museum, a conservatory, and a theater (Playhouse in the Park).
- the Main St entertainment district (Main between Central Pkwy and Liberty). again, lots of bars, clubs, and restaurants... my personal favorite for eats is the Main Street Brewery, which is a micro brewery/eatery.
- the Back Stage theater district (Walnut between 5th and 8th streets) has many eateries.
- Fountain Square also has a micro brewery (Rock Bottom) and the 5th & Vine Bar (located at street level of the Westin... the Reds Dugout Shop is also in the Westin... right across from the bar).
- If you don't want to drive all the way to Montgomery for ribs, try the Boathouse (same owners as Montgomery Inn), which is right on the river just past Sawyer Point (your hotel can give you directions).
- Not too far is The Presinct (an old police station turned into THE place for monster steaks) and Arnolds is right down the street from it (someone mentioned Arnolds earlier).
- Kentucky on the river. The Waterfront, Covington Landing, B&B Riverboats, Mike Fink's (floating restaurant), Riverboat Row in Newport, and Newport on the Levee (entertainment complex).
There are a ton of other places but these are all in or near downtown. Plus, of course, there are other good restaurants and clubs scattered around downtown.... the Havanna Martini Club, Red Fish, the Phoenix, etc. Take a walk around and you'll see several. Other than the Main Street entertainment district, I'd suggest you don't walk any further north than 10th Street.
Oh, and lest I forget... don't miss Koch's Sporting Goods on 4th street (pronounced Cook's). Most out-of-towners also don't realize there is a mall downtown (Tower Mall), across Vine street from the Westin Hotel.
I could give you more, but I gotta go watch '24'. Have a great trip.
"Enjoy this Reds fans, you are watching a legend grow up before your very eyes" ... DoogMinAmo on Adam Dunn