Almost any map or photo will have *some* common aspect that relates to current day. Right now I am working on a project of cataloging old (back to 1937) aerial photographs of the county I live in.
I use ESRI's ArcMap, a ruler, an excel spreadsheet and some brainpower. I pick sensible coordinates (PLSS corners make the most sense when available, as well as street intersections) and then locate them on a more-or-less current day satellite/aerial overlay in ArcMap. Once I decide on my corners, I just measure the physical map from each common point/corner to the map edge (twice for each corner- one for x, one for y). Then pick two points and measure between them and compare your measurements in the "real world" to come up with a scale (this is why excel is handy). Then you just go back to your GIS software and move each of the corner points the specified "real world" distance!
This DOES take time but it is probably the most accurate method you'll find for older maps (or aerials).
If you simply pick one or two points and rubbersheet or affine, you'll often end up with frustratingly bad results for these. Those advanced methods require many, many links with a higher accuracy than you'll be able to achieve. My method also has the benefit of accounting for rotation/skewing/etc (not all the aerials/maps will be the exact same orientation, dimension, and scale... in fact, it's rare that two have even one or two of these elements relatively close).
Good luck!