Anecdotally, the main trouble spots that I've heard of, have been with hot-rodded American push-rod V8 engines with flat-tappet lifters and very high valve spring pressures. And, if your engine is relying on years of sludge build-up to seal its gaskets (!) then modern oil might make them leak. If your engine is so old that it doesn't have a modern full-flow oil filter, maybe that's a problem from the detergent point of view.
Historic two-stroke Detroit Diesel engines seem to want straight-grade oil. No idea why.
I've had no issues using modern oils in vintage motorcycle engines that are DOHC with direct-actuated flat-tappet lifters, but with lighter valve mechanisms and larger contact faces than you would see with the American V8 applications. All have modern full-flow oil filters. Just stick with viscosity somewhere near what was originally recommended. I use the same Motul 7100 10w40 in my 1980s motorcycle that I use in my newer ones.
You can get motor oils designed for historic applications. They won't carry modern compliance markings (e.g. API or ACEA).