Obviously we all want to avoid enshittified (aggressively monetized) software or at least get our money’s worth. I’m looking at self-hosting software right now and one I’m looking has a pricing page but only for cloud (no other paywalled features) and is open source. I tried looking up future plans and didn’t find much, so it doesn’t seem like it will enshittify. (not related) I had thought about switching to Omnivore for a long time but then they merged with ElevenLabs and the rest is history.
Look for escape hatches. I run a self-hosted Cloudron server. The software I host on my home server is FOSS via Cloudron, but Cloudron itself is a service that keeps each of the FOSS apps up to date with security upgrades and data migrations when necessary. It’s a huge boon to running a self-hosted server.
But when it comes down to it, they could potentially close up somehow (new leadership, get bought out, shut down etc.) They’ve left an escape hatch though–you can bundle and build your own apps, with a CloudronManifest.json etc. This would allow me to continue to run and update software if I absolutely needed to, without their support.