OK, so against my advice (I told him to get a Mac), jsnydcsa Sr. bought the following from Dell.com - I've cut and pasted some of the big details.

Inspiron 530 Intel® Pentium® dual-core processor E5200 (2MB L2, 2.5GHz, 800FSB)
Genuine Windows Vista® Home Premium Service Pack
4GB Dual Channel DDR2 SDRAM at 800MHz- 4DIMMs
ATI Radeon HD 3450 256MB supporting HDMI
20 inch S2009WFP Widescreen Digital Flat Panel Monitor
500GB Serial ATA Hard Drive (7200RPM) w/DataBurst Cache
Norton Internet Security™ 2009, 15-Month, English

He already has MS Office 2007 (Outlook, Word, Excel) and is using it on an old (5+ years old, I think) Dell. He uses gMail with Outlook via POP. Wired Ethernet connection to a Verizon FIOS connection. According to Dell, he's going to be able to have a dual monitor setup using his old monitor, the new monitor and the ATI Radeon HD card. He's not doing any heavy tech lifting - just email, web browsing, scanning of docs to PDF (for storage/emailing), Skyping.

So, now, of course, he wants me to set the new computer up and move everything over (in particular, ALL Outlook data, as well as approx 20-50 Gig of documents). I have two days this weekend to do it.

Help me get this thing up and running and make it as goof-proof as possible.

A couple of concerns he's raised (1) approx three months ago, he bought (I believe at Costco or Best Buy - possibly a MyBook) a 1 TB external USB-connection hard drive which he could never get to work on the old XP machine, he'd like to use that as a simple off-site or at least, out-of-the-same-room-as, backup solution, (2) he's also considering some sort of backup to DVD solution - so backup software (freeware?) is a need, (3) he has a lot of WordPerfect files that he would like to work with (I've tried over several Thanksgiving Weekends to show him how to open them in Word or Open Office, no dice), (4) he hates, with a passion, the annoying popups on his current machine associated with McAfee (I guess that's why he went with Norton), (5) he doesn't want Outlook Express on this new computer (don't ask, long story).

A couple of things I've thought of already.

Get Firefox or Chrome (he's using Firefox) - can handle moving bookmarks/favorites there.

Get Yuuguu to connect over to his computer and remotely tutor//fix/show him how to do stuff

Get Skype

Get reid of crXpware/crxplets
PC DecrXpifier
http://pcdecrapifier.com/

Get rid of Outlook Express / Vista Mail

I'd be looking for a good free reliable backup software program
Poked around here http://www.backupmill.com/ and here http://www.techsupportalert.com/best...backup-program but am open to ideas.

I'm particularly concerned about transferring all of Outlook (emails, file folder layout, contacts, calendar entries)
Once again, FT to the rescue,
http://www.flyertalk.com/forum/trave...ew-laptop.html
(if it is that easy, thanks derekmines)
http://www.flyertalk.com/forum/trave...ew-laptop.html
(as always, the tips for the AutoComplete feature are helpful, that would be the first thing Mr. jsnydcsa noticed).
Is it truly that easy?

Couple of things that I'm wondering about
- Any tweaks to Norton (if I keep it at all) to ensure it doesn't become omnipresent/omniproblematic
- Any ideas about utilizing the 1 TB external hard drive (other than as a bookend)? Format?
- Dual monitor setup tips?
- I've seen this NYTimes Gadgetwise Blog Entry - http://gadgetwise.blogs.nytimes.com/...speed-your-pc/ - any thoughts?
- Any other ideas on how to deal with all the WordPerfect files?

On the old computer, once everything is set up
Eraser program
http://www.heidi.ie/node/6

Any other whiz bang ideas (besides . . . Bring a fifth of Jameson's)?

Cheers!