Your #3 might be the real key to all this. I rarely apply for a job cold. I've nearly always had some point of networking somewhere. Even for the job I have

Your #3 might be the real key to all this. I rarely apply for a job cold. I've nearly always had some point of networking somewhere. Even for the job I have now, for which I did just send in a resumé and an application cold, I have some very specific key words on my resumé that the hiring manager recognized and then started asking if I knew person x and person y and so on and we discovered that we have a bunch of prior colleagues in common, which also made me extremely useful to the organization in ways they don't advertise (I already knew this going into the interview, as I did my research). Finding a job is very much about market segment, branding, and networking. If you're "just another web dev" and have no other meaningful skills and no friends, then maybe finding work after 40 is hard -- I wouldn't really know. If you're a C++ guru with an MS, an embedded dev, a specwar comms tech, etc, you get really valuable to some people because you've got such a broad set of experiences, and they don't give a rat's ass how old you are as long as you can still hobble in to work some days. And sometimes they'll hire you for your network as well, which isn't all bad either.