Great. That's 2 x 6.2 and 2 x 6.3 shots of Tequila tonight to mark progress.
Chaps and Mrs Robinson, posts might get a little ugly later

DarkSend Beta v6.4 - v.0.10.3.3 (same)
- More stability fixes for masternodes

- Windows client will be pushed up soon
https://www.darkcointalk.org/threads/darksend-beta-v6.226/works
./darkcoind masternode count
4
For some reason I can't send 1000 DRK from my windows wallet... any ideas?
You're going to have to be a little more specific, what happens when you try? Can you send a smaller amount?
lol, sorry about that. I can send 2 DRK to the same address, no problem. When I try to send 1000 DRK, I get a long pause, then an error message "transaction too large". I tried adding a 1 DRK transaction fee (that would have been a fun block to find!) but still the same error. It isn't the same type of error when it wants to send a transaction fee.
Sounds like you might be using the Beta wallet and you have the Checkbox checked for Darksend, which in beta right now is limited to < 10DRK. Just uncheck the box and try.
That would do it too.
However if you aren't using the beta client, how many transactions (estimate) have you made? Would you say a lot? If so it is possible you have built up a lot of dust, and the total size of inputs required to get 1000 drk is too large. Not a common problem but it can happen.
If you have made a lot of transactions, run the command listunspent and let me know how many unspent outputs you have. (If using darkcoin-qt, go to the debug window and just type "listunspent". If running from CLI windows, "darkcoind.exe listunspent", or linux: "./darkcoind listunspent" Without the quotes in all cases.