> - an early-stage startup CTO mindset, - jack of all trades, - expert writing dirty/hacky code,
This is exactly the sort of person early-stage startups are looking to hire. And a lot of therm are going to be offering a full time job, possibly below full market rate - but topped up with equity dream-bucks.
30-60 hours at market rate per month seems quite unlikely top turn into "a long-term companion" given the other opportunities anyone skilled at all the things you're going to want will have open to them.
The prospective part time engineer you’re describing sounds to me more like what we call a Rock Star who probably has no trouble finding a full time six figure salary with equity and benefits. Not sure why they’d throw in with you vs just finding a real salary or I-9 gig, unless you are very competitive on total comp, or they are already financially secure.
I think you’re just looking for a VP engineering.
If you want them for half-time, and freelancers typically increase their rates to cover down times, sales time, benefits, etc... would you not do just as well to form a company, hire them, and give them a salary?
I'll do it. $40 per hour.
How is this not just a freelancer who you rehire periodically? Most are happy with repeat business.