Hi @PAmend1987 ,
To be clear, I would not propose updating a deal. Rather, the upgrade is a second deal with a value of $2000. The old deal still has a value of $1000 and a close date in the prior year.
Then you can create a deals report using the Company Name as the filter that shows two deals: a $1000 deal in year one, and a $2000 deal in year two.
HubSpot calculates ACV (Annual Contract Value) in year one as the one time fee if applicable, plus 12 times the monthly recurring charge. So your first contract is worth 12,000 and your second contract is worth $24,000.
If you want to understand the incremental change in revenue from a deal, I would recommend a “Prior Contract Amount” property on your deal with a calculated property to calculate the incremental change in revenue. In your example Amount - Prior Contact Amount = Net New Revenue. In this way you know both the total value of the contract and the incremental change.