Sidebar topic: (analog or digital) Work Tracking Systems for solo/tiny team sizes.

Central Question: What pragmatic work tracking advice do people have for tiny (1-4; 1 founder, 1-3 contractors) team sizes, analog or digital?

Context: I noticed a source of friction for my larger solo projects (1+ months) was a lack of structure and carrying the entire project in my head. Effective for hackathons but life is starting to force me into more context switching (getting older I guess). I've already refactored my work system to involve an analog weekly planner + weekly retro/plan ritual, heavier emphasis on digital calendar, adopting a two phase work philosophy (planning/grooming, task execution) often facilitated by pomodoro (5 minutes plan, 25 execute), and leaning on having a digital work tracking system.

I've taken a large bet on GitHub's ecosystem. Issues + "type:" labels let me create ticket types (spike, feature, bug) + "area:" labels (e.g. runtimes, category of concern (security, REST, client, ...), ...) allows me to gather and tag appropriate units of work. GitHub projects supports kanban boards and "filter by" or "slice by" features that are helpful. Pull Requests + Actions let me vet software additions. Issue/PR comment streams allow additional context capturing. Milestones & Releases let me plan larger epics and bundle my software. It's a robust digital system whose mental model makes sense in the context of delivering software.

I have an ambitious software project idea (multiplayer game software) that I'll eventually want to bring in a contractor or more. I want to stipulate some degree of interfacing with my system, even if it's just to capture the high level "this feature is handled by contractor A" and allow delegated delivery.

The points of friction so far have come from wrestling decision control with ai agents, and resisting the temptation to plan in too much detail too far into the future.

Given that brain dump, what advice might you have for me to help make for successful?