Which version of the album/single do you go for?

If you are interested in an album or a single, do you go for the original 1st pressing or the most recent one that may be better quality (my assumption given technology has progressed). Or even maybe you go for both?

I am always inclined to go for the very first pressing (for no apparent reason to be honest) which makes it difficult to find in a NM condition and quite expensive at times which doesn't allow me to buy the vinyl as a result.