You can get 5 years security updates support with Ubuntu Server LTS and you can set up safe unattended updates[1] with email notification if anything ever requires your attention. If you set your backups right as well, you can get away even with catastrophic hardware failures.
Remember, this is not some gigantic scale, it shouldn't be that difficult.
[1] https://help.ubuntu.com/10.04/serverguide/C/automatic-update...
Famous last words...
I'm not saying it can't be done, I'm just saying that my experience has been different. Another example, I used to have my own installation for our websites and bug tracking and time sheet management software, on a locally-hosted machine with apache and mysql and a bunch of other software. The number of hours I've spend migrating data between versions, tweaking mod_rewrite rules, setting up backups for various databases and other data, making usage statistics etc. - I don't even want to think about it.
Recently I moved to a shared hosting server. The yearly cost of that is covered with one hours of my hourly rate (and I'm not even expensive). I can set up 50 or so different applications with a few clicks in a web UI, and upgrades are handled by it, too. Backups are taken care of, I have a web ui for dns, ssl, everything. It was like a breath of fresh air.
To each his own and each situation is different, of course. But there's something to be said for division of labor.
It seems (from prev. post as well) like you were trying to stay on the cutting edge functionality wise. OTOH I was arguing for running stable and maintained Linux distribution.
I'd certainly agree that the initial investment is pretty big—not only it takes some time, but you need non-trivial specific knowledge about Linux administration—and for that reason alone I'd advocate using maintained hosting. My only beef with your comment was that, in theory (and in my experience), a properly configured VPS running stable software shouldn't require nowhere near the level of maintenance you seem to be suggesting.
A one-man operation doing sysadmin, development, everything? I'd be looking for hosted solutions too for my clients - it makes my life easier.
But as a company, with a development and operations staff? I'd be wary.
Actually your home desktop box should be much more difficult to upgrade than a simple generic server box with generic virtualized hardware drivers.
There are valid reasons to use service providers or maintained hosting but properly configured (and backed up) VPS running stable (& maintained) software can get you a long way.
1) get a distro with 5 years support.
2) when it's out of date, buy a new $20/month vps, install git and ssh. Move your repo and turn off the old server. This might take 2 hours, every 5 years. Not a big deal.
I've done this several times over the last 5 years and am now finally moving everything to specialized hosting services. Just hosting a web site, photo repo, mail and svn on a machine (vps) is enough to make it a serious hassle Moving all those to specialized services costs the same, is less work and more reliable.