VISA offers zero liability protection to all its cardholders if you are disputing a transaction due to fraud. It requires the bank to provide provisional credit to your checking account within 5 business days of receiving your dispute in writing. The bank then has up to 90 days under Federal Regulation E to investigate your claim. Dollar amount does not matter. The bank will only side with the merchant if the merchant can prove that you actually did the transaction.
However, if you are filing a dispute for a non-fraud reason, the answer is, it depends. Why are you filing the dispute? Canceled and charged anyway, returned merchandise and haven't received refund, incorrect merchandise received, merchant failed to provide promised service, etc... Note that "buyer's remorse" is not a valid dispute reason. If you buy something and the merchant clearly states "no returns or exchanges" and then you change your mind and try to file a dispute, you will ose.
For these types of disputes, VISA will require that you first contact the merchant and attempt to resolve you dispute with them. If this fails, then be sure to include your efforts and the result on the form supplied to you by your bank. Again, once the bank files a chargeback, they should provide provisional credit. However, the merchant can refute your dispute if they can prove that they acted in accordance with VISAs operating rules and that you are in the wrong so the bank may reverse the provisional credit.