The real trade-off
Self-hosted tools (WordPress + MemberPress, Tendenci, custom builds) offer more control but require technical maintenance. Hosted tools (Covey, Wild Apricot, MemberClicks) offer less control but zero maintenance. Most organizations should default hosted.
When self-hosted makes sense
You have a full-time technical staff member or contractor. You need custom integrations beyond what hosted platforms expose via API. You want to own your data in your own infrastructure. You are running a very large (10,000+) organization where hosted pricing becomes punitive.
When hosted makes sense
You are a volunteer board running operations on nights and weekends. You want updates, security patches, and backups handled for you. You want vendor support when something breaks. Your data model fits 90%+ of what the platform offers out of the box.
Hidden costs of self-hosted
Hosting ($30 to $200/month). Security patching (monthly at minimum). Plugin licensing (WordPress + MemberPress + WooCommerce + Events Calendar adds up). Developer time to update and maintain. Downtime during migrations.
Short answer
Hosted unless you specifically need what self-hosted offers. The maintenance tax on self-hosted is real and often under-counted.