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I will suggest that you edit the question like the following: where you're at (i.e. current physical stats/ability, any limitations), where you want to be, and finally summarize your question succinctly. The title of your question, "How can an overweight engineer get back in shape?", is different than what you summarized in your summary, "ultimate goal is sheer aerobic staying power". These questions will have very different answers! (it's ok to ask multiple questions too)
Thanks for the info. Your advice coincides with exactly with what my doctor warned me about: running with flat feet could lead to more painful injuries/conditions and the daily use of orthotics. My current goal is to compete in a 5K and then return to alternative forms of cardio as my "staple".
Full disclosure on my part, my doctor confirmed that I do indeed have fleet feet. However, I wanted to phrase this question to be generic enough for anyone to find an answer :)
Yes! (Been there done that too!!) When going back to the gym, it's perfectly ok to start at a lower weight than when you started. Don't worry though, you will be back to your normal weight soon enough :)