There's alot of reasons why something like Milwaukee Metalfest can't and won't happen now, not least of which the fact that it's gotten such a bad reputation that many bands will just refuse to have anything to do with it now. But there's also alot more competition out there than there used to be. It's pretty hard to compete with the Ozzfests and all that shit, and now you've got the ProgPowers and the Heathen Crusades and so on that are featuring some really good lineups, not to mention New England Metal fest, so there's definitely some competition these days.
I can understand to a degree the need to charge the small bands to play Metalfest. It costs a shitload of money to put on the fest in the first place. But what happened was, it got to the point where 70% or more of the bands playing were small unheard-of pay to play bands, and then the remaining 30% were the "known" acts, and even then it wasn't quite up to snuff. Alot of people didn't mind going to a fest with a couple dozen local openers when the headliners were acts like Slayer, King Diamond, Venom, Cradle Of Filth, Anathema, etc. But the last few years showed the quality of the "headline" acts dwindling considerably, and so there goes any chance of getting a real draw.
Anyhow point is, Jack should be given credit for keeping it alive for as long as he did, and for bringing many acts to the U.S. and giving them their first real exposure to us in a live setting. But it seems as though his time has come and gone now, and through poor business relations, outside competition, and other circumstances, I think Metalfest might be near it's end.
I personally think that if he were able to somehow get a couple of really good headliners with drawing power, a couple of underground bands who people never get to see here (My Dying Bride? Rapture? Bloodbath?), and then maybe have the rest of the day be the smaller to mid level bands, and have it all in one day only, it could be a success. Fests like the Heathen Crusade are shaping up to be akin to this, I think, and definitely have got the right idea!