I was seriously enthusiastic about the Transporter based on recent reviews in Stereophile, and others, especially including some very informative comments by owners here. I have already begun taking the steps to put together the funding to purchase a Transporter fairly soon, but I may be beginning to rethink the wisdom of going that route.
It would appear that there is a distinct learning curve associated with ripping, and what to rip with, and compressing cd's, and what to compress with. Add in the rather daunting fact that I would then also have 1500 cd's to rip, and the time involved..........well, I'm wavering.
Add in also having to purchase a 750gb-1tb drive to store all of this on, and an equivalent drive to back up all of that hard work and the resulting stored files, and suddenly the once approachable $2000.00 price for the Transporter appears to only represent the beginning of the expenditures necessary to pull this off. I really, really wanted to take this technological step. Having all of my music readily available, easily accessible via the turn of a knob, and reproduced with exceptional sound quality sounds like a dream come true. But gods this would be both difficult and seriously expensive.
Check out the slim devices - Beginners Guide wiki to help you up the learning curve.
I'd concur with your findings as to using EAC + FLAC as the way to go.
Try a couple of representative CD's to get the process down, and sort out any issues you may have. Correct Tagging tends to be the biggest time cost. Ripping you can do in parallel with something else - if attended, or just do it unattended an you'll get there. Remember the journey of 1000 miles begins with a single step.
If you do decide to get a Transporter, it can be used as a DAC using the digital output from a CD player, so you can still use it to listen to as yet unripped CD's.
As for storage, there's a quote that goes "There a two kinds of Hard Drives in the World. Those that have failed, and those that have yet to fail.
Storage is a commodity, and is getting cheaper. Buy the most cost effective drive you need at the time you need it. Slimserver can read music files spread over multiple drives - it doesn't have to live on one drive - that may reduce your total cost.
"How valuable is your Data?" What is it worth to you, not to have to re-rip the contents of a failed drive? Some people just clone the contents of a drive to another, then put it in safe storage, ready to replace the used drive when (not if) it fails, at which point the process is repeated.
You can also go for a phased approach to help the cash flow. Start off with Slimserver + SoftSqueeze (they are free to download). As you rip more of your collection, get a Squeezebox, then transition to a Transporter when it makes sense to do so. You would then have a spare Squeezebox for resale, or for use in a 2nd Room etc, still able to access all the content on the network.
Hope this helps.