I pretty much stick to straight bash and core utils, so it’s not much of a burden. Plus on the Linux side, I mostly stay with Debian and its derivatives, which limits some of the work.
But really I don’t consider every feature of my dot files to be a finished product. The core stuff is reliable, but if I catch a problem with anything more esoteric or if I see some functionality that looks interesting, it’s a brain teaser I get to tackle.



The way I handle this is to have two VMs running in separate hosts, each running my reverse proxy along with keepalived. I resolve my subdomains to the keepalived shared address and then keep the reverse proxy config in git with a cron job to pull updates.