I think the problem is that the original versions won't work with modern operating systems - he has the originals already.

I was actually digging around for this recently, but wasn't able to find a fixed original. I did find a version with some fixes and some changes at http://www.slightlymagic.net/forum/viewtopic.php?f=76&t=2349, which wasn't too hard to get set up (the hardest part was finding an iso mounter which wasn't super sketchy). I'd never played the game before, but everything (except random newer art sometimes showing up) seems to work reasonably well out of the box on Windows 10.

I'm interested in playing in paper old school at some point, but with no local community and no experience of the gameplay it's a pretty hefty cost for playing a couple times a year, especially when there are such disparate standards for allowed cards.

While I'm sure old school purists vehemently disagree, this seems like a decent way to get my toes wet and see if I like it, so I went ahead and put together a couple decks on MTGO since most cards are pretty reasonably priced. My MTGO username is "benbw" if anyone would like to play some games.

Has any thought been given to running these on non-holiday weekends? This one is the weekend after Thanksgiving (though admittedly it's a bit late to change now), and the December one the day after Christmas. I'd love to make it out as soon as I can, but I (and I imagine more than a few others) won't be available for these.

Hello.
I'm Ben, from Madison, WI. I got into Vintage through the VSL and have been playing a fair bit of MTGO Vintage while building towards a proxied power paper deck. I enjoy BUG Fish, artifact based blue control, and any deck with Cabal Therapy/Young Pyromancer.