I’ve owned a 1991,1996,1998,2007,2008,2012 dodge diesel and always changed my own oil and filters and every filter I’ve taken off has never spilled any oil out upon spin off and was always a little low on oil inside the filter, you are indeed worrying a bit too much. Currently I’m browsing forums for what seems like an eternity for oil pressure build up for my 1998 12valve because offhand I don’t think my 1996 takes that long to show oil pressure but every year of pickup seems to have a different personality in some regards. Finding out that it’s normal and just me overthinking once again.