Stumped? Well, sort of; third back: was out of town, second back: too generic (a zillion "lighthouse buoys it could be), first back: yeah, stumped (though remember Dan'l Boone: I'm not lost, I'm just getting my bearings) but I took months to find Cartagena. Oh, and this most recent? Yes it's "SD," and not just "maybe": see 4.bp.blogspot.com/_0ceHaR5RPhk/TTiF83B8M1I/AAAAAAAAATQ/lZjc7Y_CXWM/s0/san+diego.jpg at dict.space.4goo.net/city/100185?q=San+Diego
"...this sign?": Given that it appears to be "Darlene," of i m a g e f a p.com/pictures/4006754/John-and-Darlene-outdoor-showoffs-in-Canada , and given the other sign picture in that set, I'd say Shingle Lake, Nova Scotia (not too far from Mahone Bay, all in the area of greater Halifax); no Google Street View there, though, so not photographically 100% proven.
"...out the window" is Hong Kong, prominently featuring the distinctive Bank of China Building, as in hansens-hikes.com/Gallery/Central-Western/060221_Hong-Kong_Admiralty_Lippo-BOC.jpg
"...this bank" is the one on Plume Street, Norfolk VA; verified at Google Maps by viewing along the East City Hall Avenue side; picture most probably from the Courtyard Norfolk Downtown hotel.
Monique's picture: Yes it's 3rd and Spruce (across the street from the "3rd & Spruce Café"), but it's in West Reading PA, across the Schuykill River from Reading proper; I did verify the statue (but no Monique, sadly!) in Google Street View.
Re "Any one recognize": Tampa FL, from a parking garage along N. Florida Ave.; base of SunTrust Bank at the intersection w/E. Washington; distinctive Colonial building of Northern Trust Bank ( flickr.com/photos/12684135@N02/2457788916/ ) up the street at intersection of Madison/N. Florida.
Latest ID: Manhattan NYC; see lh6.ggpht.com/-cAD1PCZk77w/TlJqCi_pbWI/AAAAAAAABTk/2mTTefJp99k/s0/HobokenBoardwalk.JPG (from offmetro.com/ny/2011/08/22/best-places-to-take-photos-in-nyc/ ) for those two buildings -- one w/dome, one w/cranes. Specifically, picture is from the last block of South End Avenue, just south of W. Thames Street, looking uptown...
Before you ask (or accuse) about certain pics, please look through the threads here at OCC, chances are it was already posted here, and I just added it into another appropriate category
The others are found @ places like imagebeaver, imagefap, etc