Organising local transport from cities 1-5 hours away seems like a much more effective use of time and cash than shipping IWW members around the country and it'd potentially bring people into local/regional networks. Doing national travel (in the US) feels like reproducing summit-hopping dynamics.
I'm aware of how big the US is and I'm not suggesting people should regularly be flying en masse across the continent to take part in anti-fascist protests. But my point still stands that anti-fascists need to be matching the areas the far-right are using to mobilise. This is something learnt from years of experience in the UK. The times when we've had problems have been when we've only mobilised with anti-fascists from London, but the far-right groups opposing us have mobilised from London and the wider home counties. This imbalance can give the far-right a numerical advantage they may not otherwise have and means they're more likely to win any confrontations. In most cases, if the left mobilises from the same areas it'll pull enough people to outnumber the far-right and enough people prepared to defend themselves from fascist violence.
Transport can be done from cities more than 5 hours away as well. One thing we've done in the UK is doing half the drive overnight, stopping in a big city where there's networks to host people, and then completed the drive on the morning of the protest. If you're hiring minibuses you can do 10-11 hours of driving assuming you're leaving when people finish work on a Friday and arriving for a demo in the middle of the day on a Saturday. For stuff like Portland it would make sense for places like Seattle, Olympia and Eugene to be sending coaches full of people, while the Bay Area could send minibuses (although I'm not sure there's any big cities between Portland and the Bay Area which could host people overnight, I guess camping could be an option).
I think it's my fault for trying to give two different examples of anti-fascism (a trans-continental version and a local self-defence version) in the hope that the discussion could move past 'anti-fascism' vs. 'ambulance chasing' vs. 'workplace organising' into more concrete examples of what useful vs. not-useful activity might be. There's often a sense that people are talking past each other in discussions like this, but equally an unwillingness to be specific about exactly what people are opposed to.
This is a very important point and it's not just a bit of cleaning or working in the kitchens, but a labour force of around a million people (a third of all incarcerated people, and not sure what that stat was based on) working full time for cents per hour to produce commodities for large companies on contract, and one that has been regularly going on strike in the US.
Now there are liberal versions of anti-prison/anti-police stuff, like the DSA endorsing Larry Krasner for District Attorney on a reform ticket, but that's about as far from the IWW-IWOC as it's possible to get.