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I initially misread that (or at least I hope) of 100 hours/week. I’m lucky to be in a gig where overtime is frowned upon and requires prior approval/justification; this lends itself to be very friendly to writing and other hobbies. And, as an aside, you might enjoy: https://arstechnica.com/information-technology/2012/01/microsoft-pimps-it-old-school-with-a-pricey-text-adventure-game/

I’ve never had a good knack for making decent “ballpark” estimates except in the simplest of cases. And in this case, I don’t know the state of the current codebase, the state of the database, which features would actually be desired, or the modifications/rewrites needed to make that happen, so any estimate aside from “possibly major” is deceptive IMO.

Chapter Seven is up.

Correct...I don’t expect his first assignment to take 100 hours. If it does then I need to have a talk with my boss. As for overtime, we at my work have the rule that you have to explain yourself if you have too much overtime collected. We laughed quite a lot about that at work back in the days. Regional Manager was the award that collected most laughs. The actual hunt was to find a consult work we had that done not merit the achievement...it was tricky. Thanks for the reminder. In return I give you an XKCD about Bad Code https://xkcd.com/1926/

I’m not even remotely qualified to comment on what it would take to modify the current code, although I suspect it would be a major undertaking. My usefulness comes when it’s time to beta-test the updates, since I know what will work, and what will create issues for our members based on the troubleshooting inquiries I get.

As a reference at my job I am currently bringing in a new programmer in one of the projects. I expect him to spend 100 hours before he get proficient enough with the codebase to make design choice on his own. Until then I devote hours each week just to answer questions and say yes/no to ideas. It takes serious effort to vet a new programmer for serious work.