The small filter does not make sense. The Fram PH25; Delco PH24; Wix51258, etc are good sized filters. These filters fit most of the Cadillac, Oldsmobile, Buick and Pontiac V8s from about 1965 through 1976.The filters were much narrower starting in 1977 through 1990 for the BOP & Cadillac V8 engines. Since you may be dealing with incompetence at your local parts store, remember that the Chevrolet V8s of a given year use a totally different filter never shared with other GM divisions' engines. A lot of young kids at the parts counters now do not understand this.
For oils, the 5W-40 for winter and the 15W40 for summer in MA would be good as previously suggested. 10W-40 would be my low cost preference for year round- 20W-50 for summer only. If a 10W-30 is chosen, better check the zinc levels for the flat-tappet camshaft first. There are a few diesel oils still available with elevated zinc levels which would be ideal. The 5W-40 oils might be a best choice for year round since they tend to pass the cold viscometer test just well as a 5W-30 oil. 5W-30 is not a suitable summer oil for the Cadillac 472-500 engines designed for a basic 10W-40 oil grade. If the car will be outside overnight in winter, the 5W-40 is superior technology as it is only slightly thinner in hot temp viscosity testing vs 10W40 and should be excellent for pumping up the lifters. With the excellent stock oiling system in this engine and 5W-40 synthetic, all should be good. 0W-40 would be a little pricey for this six QT sump. Add dual exhaust & Enjoy your nice car. Upgrade the cam, lifters & intake and really improve things.
Dr. Olds
1994 Intrepid ES 3.5 24v Amsoil Signature Series 10W30
1969 Olds Toronado 455 HO NOS Rotella 15W-40
1975 Olds Cutlass 455 " " " " "
& more cars.