Hi Unknown,
I can't really speak about fishing for holdover stripers since I never did a lot of it.
I did a fair amount of fishing for searuns. It was never easy. It usually took several trips to get one.
Unless you were fishing during the spring or summer, or fishing with shrimp or chubs.
During those years I fished with a lot of different guys during the winter. I don't think any of them would say it was easy to take them at that time. In fact it took a lot of time and hard, painfully cold work.