I've always worn it on the inside, facing inward: I picked this up from my Dad.
Was your father in the military, perchance? Or did some kind of potentially damaging manual work? The origins of wearing it facing inwards is a military habit, especially pilots, but also in other branches, partly due to ease of viewing when flying but also to reduce the risk of damage to the glass from accidental impacts.
I wear mine facing outwards.
Of course, the other reason to wear the watch facing inwards is if you're (IIRC) Stan Laurel in that glass of water sketch......
I wouldn't mind picking up an entry-level Rolex myself.
Regular (ie non-limited run) Rolexes look nice enough but are thought to be fairly poor value for money in wis-dom (wis = "watch idiot savant"; you know the kind of guy I mean). Buy it if you really like it, though.
I've sort of gone off watches a bit. I like my current two "daily wearers" (nothing particularly fancy; an Omega Seamaster for casual outfits, a Longines Conquest for dressy looks), and don't feel a particular need to upgrade.
I think it's because the next watches "up" that I'd like are in a different price league (Cartier Tank in rose gold, JLC reverso, some A. Lange & Sohne models) so I just can't be bothered to lay down that kind of dough on a watch. Yeah, yeah, it'll retain its value pretty well, and yeah, the cost is amoritized because you get use of it frequently, but still, I always find that I'd rather spend it on bespoke clothes or something like that.