Since you refer to 'transactions and reports', I assume you are referring to accounting software - but it could make a difference.
It also depends on the kind of software licence you have. If the licence is 'perpetual', you make a one-off payment and then have the right to use it as long as you like, although there may be other restrictions, such as the number of computers you can have it installed on - and in practice it may in time become unusable if, for example, its owner stops maintaining it (or the version you've got) or it is incompatible with your new operating system. If it's non-perpetual, you have to keep up regular payments for the right to use it. Typically (but not necessarily) that's the licensing regime operated by 'Cloud' suppliers, who can easily withdraw your access. But even if you have 'on premise' software you may find it has been 'time-bombed' by its owner: in other words, it just stops working once you stop paying for it.
Arguably, the data you have stored and the reports you have created using the software are still yours. But they are no use to you if you no longer have the means of reading them! Printing everything out is one method, albeit environmentally unfriendly and storage-heavy; or you might be able to print to PDF or scan and store electronically. Many software applications will output data and reports in standard formats, such as CSV, that can be read by other software - including possibly the product you are replacing your old software with. Whatever method you use, make sure it works to your satisfaction, and is as permanently secure as you need it to be, before you relinquish access to your old software.
This question came up in a query from a few members several years ago, as a result of which I wrote a couple of paragraphs for the Institute's helpsheet on 'Document Retention'. I've just checked, and they are still there.