I can't speak for anyone else, but this one looks to be a tough chore! I will say this, none of those shown are Milwaukee Road.
This is what I've been able to come up with, so far. 1. Pennsylvania GG1 2. 3. 4. NYC&HR(New York Central and Hudson River) Class S-2 5. CUT(Cleveland Union Terminal) P-1a, rebuilt 1955 to NYC P-2b
Alright I think I got this... 1 PRR GG1 - Construction Photo 2 NH 351 GE EP-3 3 NYC 1176 Alco/GE Class T-3a 4 NYC 3401 Alco/GE Class S-1 5 CUT 1050 Also/GE Class P1-a Like Keith - the last two I had trouble figuring out were 2 and 3. First I found 3, then 2 was the last (looked like a Little Joe, but was two axles short) Amirite? -Mike
LegomanBill, you are really into this! I'm a steam nut and guessed the last one to be a GG-1. I think Mike and Keith have got it.
Mike, you were able to correctly get them all (even with the numbers to, I'm impressed), so you are the winner.