It looks like you're in the 16bit realm, so I'd stay with a JB3 or iRiver H120. I used a JB3 and it was rock solid. I also use an iRiver, but I've never tried the digital input. Due to the small size, better metering, better battery life, generally lower price, and reports of fine optical in performance, I voted for the iRiver.
seems to me if one is purchasing new gear and the cost is negligable and within ones budget that it would only make sense to purchase the product that one could use in the future if one desires to upgrade other pieces of gear. Just a thought.
Have fun making your purchase. i am sure you will be happy with whatever you decide.
I agree with you there, but I'd still suggest the iRiver or JB3 over a Microtrack. The R-09 doesn't have a digital input, so it doesn't function as a "bit bucket." While some users have been successful with a Microtrack, many others have had problems. The lack of a 2GB auto-split is an issue.
The original poster also stated he'd like to spend $250 max, doesn't need 24bit now, and is planning on an R-4 next year. I think the iRiver and JB3 are the only choices under that criteria.