i would still feel silly using stock tubes, a DLIII with v link, and not having a proper table/rack for a 70lb amp. if i had the funds for an endgame setup, it'd be a no brainer. WA5 maxed with double mighty 596's, and a PWD or M51
But... you're so close. If I'm not mistaken, you already have the HD800 inside the room. And shedding your current gears (everything must go!) could put you that much closer to your endgame setup. I'd focus on getting the Woo because many amp designs, especially tube designs, won't change too often but DACs will. Soon as you buy one and plug that sucka in, someone on Head-Fi will be sharing a link about the next hot DAC coming down the line.
Then when funds permit, get a really good-to-great source!