Trello is easy to adopt because its model is narrow: boards, lists, cards, labels, checklists, comments, due dates, and attachments. When replacing it, decide whether you want that same kanban shape or a broader project system with tasks, milestones, swimlanes, WIP limits, and custom fields. The important tradeoff is schema discipline. Trello lets teams improvise with card text and Power-Ups, which can hide process inside conventions. An open source replacement should make the process explicit enough to report on, automate, and back up without making every card feel like filling out a ticket.
Expect gaps around polish, integrations, and operations. Trello has mature drag-and-drop behavior, account management, notifications, mobile access, and a large Power-Up ecosystem. Open source options may be stronger on control but weaker on no-code automation, calendar sync, email-to-card flows, or mobile offline behavior. If you self-host, you also inherit email delivery, file storage, authentication, upgrades, monitoring, and backups. Treat that as part of the product decision, not an afterthought. A tool that looks perfect in a demo can fail if reminders, mentions, or attachment handling are unreliable for your team.
Migration usually starts with Trello export. Individual boards can be exported as JSON, and some plans expose CSV or workspace-level export paths. Board JSON preserves much of the structure - lists, cards, descriptions, labels, checklists, due dates, members, comments, and activity metadata - but import quality depends on the target tool. Attachments may need separate handling, and Power-Up data, automation rules, custom fields, watchers, votes, and archived content often require cleanup. Run a test import first, map users and labels deliberately, freeze the old board during cutover, then keep the export as a permanent audit copy.