How receptive is vB to changes and how friendly is it to the average programmer? There is no developer documentation for what I've seen, but there does seem to be a healthy community and effort here.
You can change nearly every aspect of the board and especially vb3 is very friendly to an average programmer.
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Oh, and is there any way to actually build the additions around vB so as to allow for upgrades in vB versions. Probably not, right? So whichever version of vB I start to work on, it'll be frozen for the rest of my site's existence. Oh goody. Is this a drastic thing?
If you are a bit expierienced in coding it is not problem to upgrade your board without loosing any of your modifications, there are tutorials around on this board