Interesting, I feel like HitTail's previous condition is a bit like a site of mine that has kind of been accumulating technical debt for a while: http://bitbuffet.com/

There are users, they pay my rent, they use the service. Its just... flat. A few bugs, various problems not worth the effort to rectify as a quick 1 minute Django admin tweak solves the problem.

Maybe its time to finally visit Flippa or suck it up and revamp the damn thing, any advice on going down this route?