When is the right time to explore a feature idea?

You might get excited about a feature and start building a basic MVP of it & launch, which would simply die if it doesn't get traction.

If you can wait for the community to be larger, then it would have a better chance of gaining traction, which you would miss out on, if you were to execute it early.

What things do you consider to evaluate when something is too early to execute?

When you are overwhelmed by the amount of ppl that are asking for it

As a mostly one-man company (for WIP at least), I try to be very careful not to spread myself too thin.

There are different kind of features. For example some increase the value for existing customers (Milestone feature for WIP). Others help attract new customers (Integration with other platforms). Then there are also features that help generate more revenue from the existing customer base (Job board).

Since I'm just getting started with WIP I'm focused on features that 1) help improve value for existing customers (helping them ship) and to a lesser extend 2) attract new customers (by improving onboarding flow, etc).

Expanding horizontally with features like job boards might be interesting long term, but it's important to get the core right before building on top of it.

I do not really have an answer. In theory, I should be focusing on "must haves" versus "nice to haves".

It sounds cheesy, but it's about 80/20... if you can achieve 80% of what you want to gain (more traction, more paying users, more happy users, ..) with implementing something then that should give you direction.

Find out if there is a need for a feature and check if people would want to put down cash for it. If not, wait until a larger userbase is present else give it a shot.