I couldn't have had a better weekend and a large part of it was my experience at the Iron Horse. Holy sexy hotel! We were there over Halloween weekend and I was disappointed we already had evening plans - I can definitely say that the hotel bar/lobby is one of those unique places that you really could sit down with a drink and meet people. It was packed and had a great fun but not too crazy atmosphere. Definitely where all the locals are going.
My partner and I travel a lot and I love boutique hotels. While the Iron Horse isn't cheap by any means, it definitely competes with places we've stayed that are twice as expensive. Everything was perfect and I don't say that lightly. The rooms are gorgeous with the exposed wood and high ceilings - a very non-froofy masculine feeling that is refreshing. If you are an architecture lover you will LOVE this place.
Also want to say as an LGBT person I felt completely welcomed in that regard.
We will definitely be back.
Only complaint is the valet parking is ridiculously expensive. We parked on the street for free - just make sure to register your vehicle through Milwaukee's city website so you don't get a ticket (google Milwaukee overnight parking to see what I mean). We had no issue finding a spot within a couple of blocks on Friday/Saturday nights.