If your dream job is "thousand of jobs on hundreds of boxes", why not start hacking on something like Hadoop/Hive (or any one of the other new/popular distribut

If your dream job is "thousand of jobs on hundreds of boxes", why not start hacking on something like Hadoop/Hive (or any one of the other new/popular distributed data stores) and, after proving yourself to the community, try to get a job for one of the companies that sponsors/offers support for the project? E.g. cloudera, engineyard, something like that. That way you're programming on a project that is technically challenging, more mainstream, and also a core part of the company employing you (instead of just being an enterprise IT cost center), all while leaving the business stuff to the company's sales/execs/etc. My hunch is that those types of companies are more open to telecommuting as well, which might be nice given you mentioned having a family.