Experiences do definitely vary in this regard. I live in a CA Bay Area suburb. Geographically, this is a valley, and there are a fair number of more-or-less active repeaters mounted up along various mountain ridges, and I can generally hit a couple of them from my tiny backyard w/ a 5W HT (and a decent antenna!).
OTOH, while I never got in to it, there is spectrum available to Technician licensees (assuming you're in the US) on 6m and 10m. You're not likely to get NVIS propagation there and hit more local folk that you couldn't hit w/ LOS, but that might get contacts where nothing's available on 2m/70cm, for not too much more initial equipment cost (again, assuming US and an HN user, where moving from $40 to say, $400 isn't completely out of the question).