advice on configuring a laptop windows system

AFAIK, only EAC and dbpoweramp allow you to set the offset specific to your cd drive, and are preferred by audiophiles. That is crucial for perfect ripping. No other programs have it.

I bought dbpoweramp out of personal preference, and don't mind the cost because I'm ripping hundreds of cds. I rip to flac, and make a copy in mp3 for portable listening.

I use foobar for flac playback and remote control it from my phone. Foobar requires some work to set up, especially with the "components." My DAC is the Oppo BDP-105

It has been repeatedly reported USB should be avoided to simultaneously stream onto a DAC and to connect a HDD, because of the serial nature of USB. It will work, but optimum performance is to be attained buy avoid USB for both.

So assuming your external HDD is USB, consider another HDD as an upgrade path.

+1 on the suggestion to use the ripping guide found at Computeraudiophile. I used it to set up dBpoweramp the first time and works great.

Look around for comments regarding JPlay. Many say it's the best software in terms of sound quality. It runs on top of JRiver and improves the sound, while using the excellent interface JRiver provides. However, lately JRiver has taken issue with this and a danger/malitious software banner appears when JRiver detects JPlay is also being used.

Jriver and DB poweramp is about all you can do software wise....

Just a practical consideration, I suspect that USB audio will be the only option available on your laptop as very few windows laptops have any other digital output that can be fed to an external DAC. Some macs (maybe all?) have an SPDIF output, but I've found this drastically inferior to the USB solution.

Also, ripping all those CDs will be truly painful (especially if you picked up some of them used and they're not in perfect shape), but the sonic rewards are well-worth it. Hard drive driven computer audio is leaps and bounds past any transport I've used in my system.

I've been running a PC front end for over a year now, and I second the comments regarding Jplay, I wouldn't use a computer based front end without it. It is a must have on a PC based system, made a *huge* improvement in sound quality on my rig, one that was immediately apparent. Jplay can run in Jriver and Foobar, can also play with iTunes but the two don't play as well together.
Also consider using a USB converter and buying a less expensive DAC, but one that still accepts high res input. In my experience this route usually yields better SQ than buying a USB DAC. The best shootout of USB converters I have read on the 'net can be found here:
http://www.computeraudiophile.com/f6-dac-digital-analog-conversion/15-usb-spdif-converters-shootout-15327/