Governance\Architecture guidance

Basically, I'm getting hung up on when is the right time to push back on a requested change? I've been working with NOW for about 10 years now, and was doing Remedy work before that. I enjoy building, but I know that making a lot of changes is not a great move in the NOW ecosystem. Skipped updates, slow upgrades, performance impacts, etc. lead to platform issues that probably end in a green field situation. I don't think we're anywhere close to that but I really want to stay away from even getting on that path where I have to unwind things. I'm already dealing with it a bit because of some of my predecessors. Not that everything I do is great, but I'm trying to do it right.

I don't get a lot of asks to widely change the platform, but even little ones add up. I have one that I recently did to adjust how the recent task/interaction queries function with the Record Information section on the workspace. It took a bit of work, but it's behaving as requested in our dev space, but I feel like it's a bit of tech debt and I'm not sure if I really want to implement it.

I've been looking at some governance threads here, but it didn't really help with this question. Though, we could definitely use some of that. We're a small shop, so it's kind of hand waved away but I believe that we're in more danger because of that position.