:) The question was hypothetical. Besides being of interest to any small cash-strapped startup, your answers are being used in the construction of an AI system. Knowing the factors that are most important to a venture's contributors will help us determine an algorithm to value the contributions.
So, basically, you don't have an alpha version of anything, you don't need a 20% development push, and you're not looking to gather 4 more people. Do you folks have anything to do with YouNoodle, perchance?
In one ongoing series of consumer products, my several-hundred-thousand-line codebase lasted for well over 10 years. There was no reason to mess with it. Yes, I thought parts were messy... but there was also great stuff in it that I'm very happy survived intact.
Then decades later, on an entirely different product, in a different business...
We had to migrate our product to a new OS platform, as well as needing to fulfill much wider requirements for our customers. The existing code just wouldn't allow this, even if it were stretched and stretched.
So I rewrote most of the codebase.
In some ways I was tortured knowing we had a functioning product that already handled things I was rewriting (even though it was on an obsolete platform). Especially since the rewriting process takes longer than zero.
On the other hand, the new set of code turned out smaller, simpler, more reliable, much more flexible, and is now working well as a foundation our for business.
Both sides of the argument make sense to me, I think it just depends on the situation.
I agree: overnight success may be programmed over a weekend, but it also has to be grown with care like a garden.
I've heard "buy some customers" a few times myself, and while it's possible for me to think like that, who as a customer would want to be treated that way? Not me. This article is an excellent, level-headed summary.
2. How would you determine how many dollars you helped the site make?