I've been helping out a friend's office recently and their books are a total mess. Some checks entered against invoices, some not, accounts receivable and accounts payable are totally unorganized, nothing reconciles...

So here's a recommendation - it's probably better to keep all your receipts in a folder system, along with records of your bank statements, and do nothing in software until you're totally committed, or can hire a bookkeeper. You can hand the receipts over to a professional a little later, but handing over a half assed mess in Quickbooks or whatever is much worse IMHO. Just don't wait too long to find that bookkeeper :)

Also, if being generally organized and fastidious is not one of your skills, bookkeeping is probably better handled by someone else, whether you have a great accounting tool or not.