I ran into the same problem getting my contacts up to Gmail. CompanionLink makes an excellent product (
Google Android sync). I followed Google's instructions but if I had a contact with only the first name it did as you and others said - orphaned the number. CompanionLink brings it over cleanly. The only problem I had was numbers listed as "other" didn't come thru. But everything else ("home", "mobile", "work",etc) uploaded fine (to get around this I just changed "other" to a valid field).
It also syncs your calendar. And you can set the interval - as short as 15 minutes. So you can change or update an email address in your G1, knowing when you need to send that email via your POP3 account in Outlook it will be there.