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I don't have anything that I deeply regret, but I have one where I somewhat regret my techincal decisions.
It was for a programming language that I developed at the time called OwU[0]. It was supposed to be a sort of mashup between Lisp and K (an ASCII-friendly dialect of APL). I took a lot of design decisions from oK[1], a K dialect with a code design that I admired.
The biggest mistake that I made during my decisions is to seperate between verbs and user-defined functions. This is because in K, verbs behaves like operators, while functions behave like, well, functions. But in Lisp, both built-in and user-defined functions should be fundamentally the same in data type.
Because of this seperation, it was very hard for me to implement functional programming stuff, like fold and reduce, because I have to handle two different data types at the same time.
Not to even mention the fact that I chose to go with objects in the entire language to be dictionaries, and not classes (I implement this in Python). This makes code just generally very messy to me, as I have to figure out how would I access the data to perform operators on them, and this cause me to make a good few bugs.
Overall, OwU is a language that is better than any previous attempt, but there's still a lot of it that I regret.
[0]: https://github.com/HoangTuan110/owu
You're right. It's mostly nostalgia value :)
ES3 is nice, and short of prayer or sacrifice one was able to import Crockford's JSON library and Ramda. Server-side Node.js without npm (for better or worse).
VBScript is less painful with aspunit [1] and plenty of comisseration/resources with drian bamaged [2], aXe, and even [3].
It was amazing how much could get done with Microsoft SQL Server, a loop, and Response.Write(). Enough to build a company and to get acquired, even. Could have been a right place/right time thing for the owner.
[1] https://github.com/rpeterclark/aspunit