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Once I buy the software am I able to update the database for future stamp issues, in particular the newer Scott #'s?.
No. However you can buy the year updates.
I assume the following is still true as I have not seen anything different over the last number of years.
If you decide to change programs in the future, it is slightly difficult. The program is proprietary so you can't just grab your data and move it. You will need to contact the owner of the program and get him to release your data in a format that you can use. Others have done it so that is not an issue but just an extra step in the process.
Stamp Manage does not have that issue.
I own and use the first program.