I've tried at various points to try some classic CRPGs, Arcanum, Fallout, Baldurs Gate, Planescape.

But while I see what might be good about them, I have difficult understanding them, coming from the more JRPG background.

If I'm wanting to ease myself into the genre, what would be the best way to go about it? Assume endless budget, all consoles, unlimited time, none of which i have but assume them anyway.

might and magic 1

This one might be something of a good transition for you:

http://www.gog.com/en/gamecard/septerra_core_legacy_of_the_creator

There's another thread here called Ultima 4 free, and a link to Joystiq to download the game from their site. I'd suggest picking that one up, and it has a lot of elements found in JRPGs, although the graphics are horrific compared to anything out today, and may be too basic even if you're a fan of the old JRPGs like Phantasy Star and the early Final Fantasy titles.

Try hack/slash rpg like Diablo, Sacred, Torchlight or Divine Divinity maybe it's a good start.

Forget hack and slash imo.

I think you should go for the FPP ones, i.e. Deus Ex and Vampire the Masquerade: Bloodlines. If going for the latter, make sure you get the community patch. The changes are huge and it is still in constant development.

I would advise against using community patch for first playthrough. if it only fixed the mistakes then that would not be a problem. the patch changes a lot of things besides fixing some minor bugs still left after official patch.

get bloodlines. you can't go wrong with that decision but don't install community patch during your first playthrough.

and don't choose malkavian and nosferatu at first. Great classes but nossies are difficult to play and you will probably miss lots of stuff. Malks are extremely fun to play but not a first as their weirdness will just baffle you while if you already know what future of game holds then you will benefit way more from weirdness.
My second playthrough with malkavian female who runs around with an axe or huge hammer is one of my fondness gaming memories I have.

...
I want to play bloodlines now.

Not to trying to be a douche, but this is TERRIBLE advice.

The community patch comes in two forms - regular and "plus", the former fixing bugs and the latter restoring unfinished content and introducing changes / balances. The former is an absolute necessity, the latter is optional.

All of this is very well explained in the installer.

im sorry but you are wrong. bloodlines 1.2 is stable and I managed to play it without problems whatsoever. wesp's patches move stuff around and do hundred other things. I have not been keeping up with bloodline community in past two years or so so the extend of changes in both patches is not known to me.

Nevertheless they do change stuff tough so playing with unofficial patches is not recommended for the first playthrough. game is stable and runs without any major problems.

The first "western" RPG I played which gave me a somewhat "JRPG" vibe was Knights of the Old Republic, so I thought I'd recommend it. Unless you can't stand Star Wars. Jade Empire is also a nice choice, but more action-y and not really party-based.

hmm. true that. last time i installed the patch the version which supposedly correct only bugs still moved crap around like the best katana from the game. I am always against mods/non-bug-fixes with games you play the first time. Knowing wesp and how often the patch changes I should have not spoken.

sorry.

I highly recommend my two favorite CRPG's. Titan Quest, and Risen.

I'd say start with a Diablo clone, like Torchlight or Titan Quest, and then graduate to Divine Divinity and Might & Magic VI. From there, the sky's the limit.

Are you people seriously forgetting Anachronox - the most JRPG like of all western RPGs and one of the best.

Blue Dragon mixes in some more western RPG elements while still remaining a JRPG.

Fallout is honestly so short and easy to get through I'm surprised you have had trouble with it. That would normally be my other recommendation.

Mass Effect is RPG-lite, and it's pretty fast.