This site is still on VB3 because of the large number of custom mods that would take hundreds or thousands of man hours rewrite for VB4 or VB5. With major upgrades, you can't simply fix the code, the majority of it needs to be rewritten from scratch.
I can't help you on the responsive question, but our site started the upgrade process from vb 3.8.7 to vb5 about three years ago. We needed to first upgrade to vb4, do a bunch of infrastructure stuff to get ready for vb5 and then upgrade. It was a long process, but in the end worth it for us. We had very few mods on our site and now only have one, Tapatalk. Only you can decide if upgrding is worth it for you and if you have any mods on your site that aren't now part of VB5 you need to find replacements or accept that loss of functionality.
You will also lose your styles upgrading from 3 to 4 or to 5.
Finally, users are notoriously change adverse. Going from VB3 to VB4 isn't a huge change from a user standpoint. VB5 is a significant change and you will both be praised as a hero by some of your members and condemned by others.
Good Luck.
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