I live in Boston and am relatively new to geocaching, so most of my geocaching is done in urban areas. The urban areas are interesting, but with the high traffic the spot usually has to be pretty good and/or maintained often (I see a lot of caches that get taken down). Also, as a searcher I find a lot of what defines a good spot is the muggle quotient. Low muggle areas are usually sketchier and if someone does come around (had a security guard come by) you tend to be the one looking sketchy. High muggle areas obviously make being discreet near impossible and you run the risk of endangering the cache. Plus off hours that might reduce muggles are usually closer to dusk, which of course compounds the issues.
As someone who wants to start placing some caches in an urban setting, I was wondering what others might suggest as a way to minimize these types problems, as well as others (short of doing a webcam or virtual type cache).
Thanks ahead of time for any ideas.