Everyone who founds a company needs to remember that they're building a system of systems that all interact and influence each other, and you have to balance short term cash flow against long term strategy.
It's not uncommon that this maintainer actually wants to get away from maintaining this code, and would actually be quite willing to teach some successor how everything works.
The problem is that it is often hard to find someone who is similarly passionate about this system (often the system only keeps working because the original maintainer invests a lot of energy into keeping it alive), and is thus brutally willing to learn this system inside out. You can't force this mentality from above: either a suitable programmer has this mentality or he is typically not suitable.
I've certainly inherited and also caused these problems in my younger years.
People running businesses want to focus on their core business and are happy to pay for pain points to go away, for money to come in or less money to come out. It's that simple.
I think GenAI opens Pandora’s box and all of these decisions change.
Theres a whole lot between "I waste my time and do non-scalable things" and "I need an enterprise contract as a SMB".
> Shitty python script with DuckDB running locally on laptop, can get you long long way.
Yeah ... no. You do you, but if you want to get your business to a good size you need proper tools. Like a chef needs a good knive, your business needs good tools as well. That's not to say that a quick DIY integration is off the table, but the one thing you don't get back is time, not money. So when you waste time by doing shit that can go away with minimal investment, you're preventing your business from getting traction.
Sorry but that's a coder mindset. "I can do this myself". That's what's keeping you stuck. You need to think about every decision as an investment. Time vs money. What's the ROI for all alternatives? Then you decide on what moves the needle. It's that easy.
The calculation is simple: every minute you do stupid stuff like coding shit, you can't sell to someone paying you to make things. So you lose twice by doing something yourself: a) you can't sell your services or time in the mean time and b) you add complexity and maintenance to your very complex business life as well. For me, the biggest problem is too much to do and not enough time. So to scale my business I need to reduce complexity. If I can throw reasonable money for that to go away: good, I'll do it. Most business owners I know think like that. That's business, not sales.
There are so many good SaaS for cheap or even with a good free tier that get you started that it's just incredibly junior to just build it yourself.