There should not be any probs overwriting your saves, but for safety reasons leave the first, working , save as is. Then make a Buck02 save which you can then overwrite.
Personally I have had problems after overwriting the same save file several times.
Therefore I tend to make a new one whenever something important has happened since I last loaded the game. If I have only "cruised" I overwrite the save I loaded from.
You should never delete old saves from your active career, never. If you try to do that, from within the game, you will get a warning that any saves after the one you are deleting will be deleted too.
Old not active careers yes, if you delete the whole career.
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