Seaside has a fairly elaborate app configuration system with a web UI. [link|http://seaside.st/Documentation/ConfigurationandPreferences/|http://seaside.st/Do...onandPreferences/]
You could trap db connection failures and send the user to a "please set up your db connection" page, get the info, and modify the method that returns the connection config and save the image. This is typical.
As for updates, most of us are using Monticello which does differencing and has a nice merge tool. There is a component called WAVersionUploader which allows you to download incremental updates from a server. Its all there and pretty sweet.
A new project designed to provide stable urls for published resources has just started, this is, I believe, your biggest objection to seaside and is being addressed for apps that are more like iwethey.
FWIW, big river books urls are like a combination IWETHEY url with a bunch of seaside type state tracking stuff tacked on at the end.
for instance
ttp://www.bigriver.com/exec/obidos/tg/stores/detail/-/toys/B000096L5J/ref=pd_qpf_gw/104-3225208-4242306
You can delete everything after the B00 bit and the url will still work, its stable up to then, the last bit is session tracking info. Seaside is doing something similar.