Google Earth/Google Maps is a great tool. I used them daily as an HEMS pilot, for lots of things, usually verifying coordinates of patient pick-up and receiving facilities, checking coordinates of proposed education/public relations locations. Google Earth is limited when it comes to topo information, but Google Maps is a good crossover for that, and there many good online topo sources.
Flying for pleasure would be more limiting in options (I guess- I've never done it) for unimproved landings, but that is exactly what helicopters are for. Pick likely sites, do an online review to determine ownership, see about getting permission is a little more involved than formal landing sites, but it can usually be done.
I hate urban helipads, the terrain is more difficult and the neighbors, looky-loos and NIMBYs can be a problem. Lots of helipads, heliports have noise issues with neighborhoods. Security can be an issue, as well, even at heliports, helos just seem to draw crowds.
P.S. Get some specific training in rooftop ops. They're usually not as technically challenging as mountains, but they have some potential 'gotchas'.
Edited by Wally, 29 December 2018 - 13:25.