Hi Freemoney,
I think it is unlikely because of the checks being made.
The only way to permanently lose bitcoin is to lose your private keys.
If you create a new wallet it will either succeed (new key written to disk ok) or fail (user gets error message).
When you are creating new private keys MultiBit checks that the wallet has not been changed
before it adds them - it keeps a running check on date and size of the wallet. If it sees the wallet has disappeared it won't write any additional private keys. If you managed to wait until the check was done and then the millisecond later managed to remove the USB drive then you would get an error message that the wallet was not written.
There is already an issue raised to give more protection to if people simply remove a USB drive :
https://github.com/jim618/multibit/issues/40It gets a bit clumsy if you save it somewhere else as now you have 'old wallet on USB drive' and 'new wallet saved somewhere else'.
The checks on date and age are also there to protect against multiple processes/ MultiBits writing to the same wallet (say if it was on a network drive). I don't really want MultiBit to 'work' very well in these situations as it encourages people to do it and you are really in an edge situation at this point. It is safer to say "Something has happened to the wallet but I don't know what (out of my scope). I won't write to it any more". Sometimes it is better to fail and stop rather than push further into the unknown.
edit: a further complication is that dirty wallets are written when MultiBit shuts down and the user interface may have gone. This makes it unreliable to solicit information from the user - the computer may be shutting down and so you just want to write out the wallets straight away.