I'm considering how to make all PRO features available in the free version, and don't bankrupt :) We're working full time on this project so we need to earn money.
There's not enough info to make any assumption, but often times companies want the convenience of a cloud-hosted solution and/or want to pay for support/priority fixes if they go the self-hosted way.
What I'm trying to say is that at your stage managing a single codebase instead of 2 might be easier, and perhaps your paying customers will be exactly the same. You should validate/ask them.