Oil filter adapter vs remote oil filter
I've had headers on my 69 340 dart since I bought it in 1981, never had an issue with changing the oil. Oil drips on headers when pulling the filter off big deal, thats what brake clean is for.
Filter is tight and hard to get off, quit putting in on so tight and oil the seal before putting it on, it just has to be hand tight.
my owning a Vintage Mopar is not for a whiner like you, Just Say'in..
And as far as the remote filter, that is just more places for a hose to blow and loose all engine oil