Hi Chris Milikouris,
Thanks for sharing the details and scope of your historial transaction.
I learned many lessons in past while migrating transactions from legacy systems but Let me share with you my recent experience. We migrated last 4 years GL transactions(Expenses and cash entries) along with only OPEN customers/vendor document/invoices from AR and AP modules. And honeslty speaking, it's become our nightmare to reconcile the balances. Actually on real ground, it's not only about migrating data from any data management tool but the most critical element is financial reconciliation of this data which is time consuming task and at the same time to ensure and verify many check points. Who will make sure that that provided data is correct.
If i tell you on high level, you have to put following check points:
1. Verify Customer/Vendor ID
2. Verify invoice amount
3. Verify currency
4. Verify Exchange rates
5. Verify Account string (Main account + All required financial dimension)
6. Verify discount
7. Verify payment references (Like check numbers/Wire/ACH references)
8. Verify tax amount/percentages
9. Total count of invoices/payment in each month to match with legacy system
If you only missed one financial dimension or used wrong GL account mistakenly, an entire reconciliation will be out and you will have to spend number of hours to find such GAPs. I'm giving your very simple example.
And even After migrating historical transactions, you have to make sure your Vendor/Customer aging reports closing balance is matcing with GL ledger. In addition to that you have to ensure all vendors and customers Invoices are properly settled with payment transaction otheriwse you will find discrepancy for individual customer and vendor balances. You have to run year end closing for all years one by one to bring the correct opening balance. You have to make sure your Asset rollforward report is showing correct values or not. There is a bunch amount of work to be done so eventually my recommendation also would be not to go with this route as Andre and Ludwig mentioned.