Do I need to buy individual ios developer subscriptions for the members of the team, if I have a company subscription

A big problem with trying to be tricky is you never know when/if someone who purchased your app will run it again. I am assuming you don't have some sort of registration involved with your app where you have contact information of your users, that would be too easy.

Probably the best way:

• Introduce a new version that is free and keep the paid version. Some people might prefer to buy it outright in the future. Downside is it splits your "popularity" between two copies, but upside you get more hits in search results. You may want to differentiate them by name somehow, but if the free one upgrades to full functionality then avoid calling it "free" or "lite". While you are maintaining two apps, they can share 99% of the same code.

Every other solution I can think of would either be a lot of work, or have the potential to leave a lot of users out.

The simplest way is to get two user accounts on the Macbook and switch between user sessions whenever you want to switch between work project and hobby project.