if you sell things on etsy, or other handmade/vintage shops, then you're familiar with the one burdensome task of keeping track of your inventory, your expenses and reporting your taxes. i am such a spreadsheet person that the thought of keeping track of everything actually excites me. however, after about a month, i wanted to kill my spreadsheet. after doing a little research, i came across outright, which turns out to be the best thing ever. it's so simple, yet so clever. you just introduce outright to your paypal account, they make friends, and you never have to do anything else ever again.
first, in order for this to work completely automated, i make sure that ONLY my business transactions go through my paypal account. no personal purchases, no personal money in. i use my account to make all of my supply purchases, pay my etsy fees, etc. i also requested a paypal debit card, which i make all of my in-store purchases, post office mailings, etc. you could also have a separate credit card that you make business-only charges to.
second, outright meet paypal. paypal meet outright. login to outright and connect to paypal. every transaction through paypal gets imported into outright and once you define a transaction into a (tax) category, outright learns and then automatically assigns future transactions in the same manner.
that's it! then outright gives you reports, tells you how you're doing in sales (income vs expenses; by customer; by month, etc). and at tax time, they give you a handy printout that has all of your expenses, income, etc, all categorized for you and even tells you how much you owe (quarterly). magic!
one other thing...i also learned about shoeboxed when i signed up for outright. for the 1% of my expenses that i can't buy on my paypal account/debit, i take a picture of the receipt, upload it to shoeboxed, then outright also imports my shoeboxed expenses (and has a link to the receipt). so, if i ever need to pull up the receipt, i have an electronic copy of it.