Here's what I'm thinking (mostly decided). The value of the Crack is that you get an awesome amp for very little money due to being a kit, and it can be upgraded. If I have it built for me, I've negated both those pros. I looked briefly at amps in the $500 range, but that would kill my budget for the DT990s.
If I get a DarkVoice 336SE, I'm still within budget and it should sound better than the SS I've been using. In the meantime, I get one of those toy soldering kits and workout whether I can solder with either double vision or no depth perception (or I can practice on some old mobos I've got laying around). This gives me an amp I can use right away, money I can spend on DT990s and time to practice/learn soldering. If the surgery worked and my double vision gets better, I can build a Bottlehead in a year and sell the 336SE.
If anyone has a better idea, I'm all ears, but I think this is my best bet at this point. Are there any other $300 amps I should check out, or is the DarkVoice my best bet? Thanks.