I use a site called NETR Online • Historic Aerials and it allows the overlay. It really to helps to have a fixed object to be able to judge distance. Good luck.
Quite frankly, those two resources (Historic Aerials and Historic Mapworks) are absolutely useless to me. Perhaps if you live in a large, metropolitan area, where people will fund map-making and organising projects, then you can find some helpful stuff. Historic Aerials doesn't have any aerial photographs of my area prior to 2004. They have tons of topographical maps, but those tell me only the least helpful kind of information in the tiniest amounts. I think I once figured out exactly how to use their system to get an aerial photo from 1993, but that's the best I've been able to get out of them. As for the Historic Mapworks, they have only one map of this area and it's the same useless map that's posted everywhere. It's an artistic map (drawn at a severe angle) of what we now call the historic district, so, even if the map was functional, I couldn't detect there anyway.
I've just about given up on maps and aerial photographs. They're just too hard to find and, once you can finally get ahold of one, the detail is never fine enough to really help. You'll end up just eyeballing your way over the ground like always. Besides, there never was a time in history when map-makers cared about poor people. Most of the buildings and population throughout American history were never mapped at all. Buildings in cities were mapped for organisation, tax, and insurance purposes. Out of town, there were "maps," which gave general indications of things, but never fine, exhaustive detail, and they were never archived (much less digitised). Perhaps you could use an old aerial photo to prove that there was once an house near a certain location, but I wouldn't expect to get more information than that.