I'd say that medium sized sites are more troublesome in that regard. Once a site has grown big enough to become cumbersome for one person to manage, but not large enough for most to justify staff, then you have an issue. There shouldn't be any excuse for a small site to fall behind with updates, etc... It's simple.
Absolutely. This is the typical problem of small-medium sized shops everywhere around the world. If you're just a really small one-man army, big companies don't really care. If you are getting bigger, suddenly you will find competition and a lot of regulatory burden. (Most startups usually fail at this point as far as I know.)
