Answer to: How should small but highly requested features be prioritized in technically driven B2B products?

The cost of this type of "customisation request" isn't so much in the work required to implement, but the on going support of the customisations over time. Your product can soon evolve into something where 90% of your dev effort is in tweaking, adding and maintaining the various customers individual custom features. This can be expensive and at some point they will switch to a competing product which offers those features "out of the box" and promises "user controlled customisation" with zero cost and immediate effect. (Whether that's true in practice or not) What you should consider with these requests is not so much the benefit for the individual customer making the request, although this may be the priority early on when you have one or two main customers, but on the features offered by your competitors. You want to make the product that people want to switch to. Not the one they are tied to but hate. So prioritise the features your competitors offer and implement them in a way that exceeds that offer, while keeping the maintenance cost lower. Rather than constantly adding piecemeal customisation to v1, consider making a v2 you can upsell to your current and new customers