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Painted Into a Corner

I feel like I've painted myself into the proverbial corner with my current web hosting. When I joined GoDaddy in 2004, I spent a long time getting Community Server running. It wasn't a supported application at the time and I had to make a bunch of code changes to get it to work in their environment. Over the years, I've made even more changes to add custom features like the Facebook status, moblog photo display, and other things. It all works smoothly with no hiccups.

But...

I'm basically stuck with this setup. My account is running ASPNET1.1 (current version is 3.5), SQL Server 2000 (current version is 2005), and Community Server 2.0 (current version is 2007.) None of those can be changed without breaking my existing blog setup.

Theoretically I don't need to change anything, but I know one day GoDaddy is going to get tired of keeping licenses for SQL Server 2000 or they'll stop supporting ASPNET1.1. Plus there are a lot of great features in the newer versions of Community Server that I would like to use.

So the question becomes, do I follow the "if it ain't broke, don't fix it" advice, or do I carefully figure out a good migration path now while I have the time? Since 2004, GoDaddy has started supporting Community Server and for most of that time, you could have them install it at no charge. In the last couple months they have started charging for it, so that means I'll have to install it myself again. That's at least a solid week of work and it's very frustrating.

ARG. Decisions.