Run the Vista upgrade advisor, if you have not I'll post the link later. If keeping your programs and settings is the most important thing to you then only an upgrade will do the job.
A clean install will give you Vista, and there are some advantages to a clean install, but you will need to reinstall all your programs and settings and files. I did an up grade and it went well.
I do not know quicken but it's worth looking at the web site for it to see if it's Vista compliant.
How old is your laptop, how many extra programs have you added?