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I am currently using TextPad Version 5.4.2.

I want to purchase a license and upgrade to the current version of TextPad (Version 8.8.1, 13-Jun-2021), and I had a few questions.

• 1.) I expected to first upgrade to Version 6.5.0, then to Version 7.6.4, and finally to Version 8.8.1 . Is that appropriate/recommended, or should I just go straight from Version 5.4.2 to Version 8.8.1?
  
  2.) Will I be able to use the Newly Purchased license on all of those TextPad Versions?
  
  3.) Will configuration setting changes I have made (Configure -> Preferences) be carried through to Version 8..8.1?
  
  4.) I use Workspace files ("*.tws") a lot (created with TextPad V 5.4.2). Are there any changes to the format of the "*.tws" files? Will I be able use these existing "*.tws" files with any/all of those versions of TextPad? Fowrard/backward compatible?
  
  5.) What is the filesize limit of files TextPad can edit? Does it vary significantly across TextPad versions?In particular, can TextPad handle editing files up to 4gb in size?

1) There's no point upgrading to 6.5.0 or 7.6.4 unless you just want to stick with the free upgrades (which you could have done any time in the last 10 years!). If you're happy to pay for Version 8, it would be simplest to upgrade directly to 8.8.1.

2) If you already have a licence for 5.4.2, you don't need to purchase one for 6.5.0 or 7.6.4.

3) They should.

4) I'm not sure, but I doubt there would be any issues.

5) The specifications state "It can handle file sizes up to the largest contiguous chunk of virtual memory". I've been able to edit files 2.5 GB in size.

You can install several versions of TextPad in parallel - you're not bound to only using one version. Just use separate installation folders, of course. That being said you can easily download the current version and try it side-by-side, especially loading your "old" TWS files.

3.) Don't rely on it - who knows what has changed since then. But having two versions side by side should it make easy to just compare all the settings.

5.) Of course, this is only possible when using a 64bit version of TextPad. Using 32bit (even when having 64bit Windows) will limit that to 3 or 2 GiB. I never edited such large files, but just reading about 3 GiB files was fine for me, too.