Bitcoin does not magically become lost. A double spend created by you does not mean that you have lost your Bitcoin. It simply means that your second set of transactions spend from the same inputs as the first set of transactions. Because both spend from the same inputs, the transactions conflict and are thus double spends. Only one transaction out of a set of double spends will be able to confirm. Once one does, the rest of the transactions become invalid and can never confirm.
One of the double spends will either confirm. The Bitcoin will either end up with whoever you sent it to, or back to your original wallet when the network "forgets" about the transaction (although this takes a few days and people constantly rebroadcast other people's transactions so the first scenario is much more likely).
That your wallet says "negative balance" and gives you errors has nothing to do with Bitcoin and everything to do with a poorly written and designed wallet software.
You said, "It simply means that your second set of transactions spend from the same inputs as the first set of transactions. Because both spend from the same inputs, the transactions conflict and are thus double spends."
I have almost the same problem as this. Has it something to do on the amount of the latest total BTC inputs againts the amount of BTC that was/were sent from it? Say for example the sender received two txns (i.e., 0.1595358 BTC and another 0.11344768 BTC and all were Confirmed) totaled 0.27298348 BTC, then he sent 0.26 BTC to other person's wallet..
And with some glitch (like maybe of his wallet provider slow relay of txns or delayed broadcast), with him unknowingly, he still sees enough balance in his wallet (previous output not being updated) so he made a second txn and sent to me 0.198 BTC..
After few days, his balance went to negative and both of his outgoing txns were flgged as "Double Spend"..
The 0.198 BTC which i supposed to received is still Unconfirmed and was flagged as "Double Spend", much the same with other receiver's 0.26 BTC
So may I ask, has it something to do with the outstanding balance of the sender's BTC wallet against the amount of the BTC sent?