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A couple of commments, if not answers to your questions.

I've been very happy with E-Trade for several years. For DRIP investing, I imagine they are hard to beat. You can reinvest your dividend at no charge witn almost anything that pays dividends. They say there are somethings they can't automatically reinvest, but I haven't run across any yet.

As for Quicken, no, it's not necessary, but it makes things a lot easier. You can use a spreadsheet, ledger, or whatever. I've never used MS Money, but probably one is about as good as the other. It's up to you, but I'd have a hard time getting along without Quicken.

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