Hi, CDavey.
Wow! How much data do you have to enter?
If your finances are like mine, it might take months or even years to enter more than 7 years worth! But if all you must enter is a monthly paycheck for income and a single "miscellaneous expense" category to record that you spent it all, then I guess it could be done quickly enough.
In other words, there's no way that we can answer your question without some idea of your personal finances.
Ordinarily, it's best to enter Quicken data chronologically, reconciling periodically as you go. It is theoretically possible to start at some arbitrary date, like 1/1/07, and then later go back and enter transactions leading up to that date, it's very hard to get the 12/31/06 ending balances to agree with the 1/1/07 beginning balances. But you may be much less fussy about such niceties than I would be.
So, in your case, a workable plan might be to first create a new Quicken file with a 1/1/07 starting point and enter all your 07-08 (to date) transactions, just so that you can file your 07 tax return. (You didn't mention any other years, so I assume they are all in order, taxwise. Where did you get the data for those tax returns each year?) Then, revive your
2003 file and chronologically enter all the transactions since then up to
12/31/06. Reconcile any differences between the end of the revived file and the beginning of the new file, then merge them into a single continuous file by creating the new file and importing from both of the old ones. Keep both old files intact until you are sure the new one is complete and working properly.
For the simplest tax situation, you don't need Quicken at all. Just hand your "tax prepper" your 2007 W-2 and tell him/her to use the Standard Deduction.
For any but the simplest financial situation, this could be a very long, large and tedious project. If you need further help or advice, please tell us more background information.
Good luck!
RC