1)My accountant is not into stocks (keeps all his $$ in t-bills) and now that I'm investing and trading on my own he's not as helpful as I'd like. How does one find a good accountant! Word of mouth or is there some sort of credential one should look for to assure the person has really good training?I'm also in the same boat of looking for someone to do my taxes this year. I intend to rely heavily on word of mouth and ask some of my friends who they use or recommend. I also intend to interview these folks to make sure that they will mesh with my style and that I feel comfortable working with them. I'd suggest you do something similar. 2)Also. I've made some $ this year, and lots of trades (my first year trading and I wanted to let myself experiment a bit so traded more than I will probably in the years to come...) I'm really busy, not familiar with Quicken, etc., and I've made enough profit that I'm wondering about hiring someone to tally up my trades, dividends, etc. Would I ask an accountant to do that or would I try to find someone with bookkeeping background who wants a few hours of extra work? I know these are basic questionss but I've never been in this position before of reporting cap gains and losses... I'm spending a lot of time on learning about the markets and prefer not to have to also spend lots of time doing the accounting as it's not my forte and I want to make sure it's done right. I think it would cost me more in time lost to do it myself than to have someone else handle it, at least this first time...I see no value to hiring someone else to tally it all up. Your stocks [if you hold them in your own name] or your broker [if you hold them in a brokerage account in street name] will send you statements with the dividends tallied for you already, and they will also send that information to the IRS. As far as the trades, you should have the confirmation information from the broker for when you sold. I would gather the whole thing and give it to the accountant to include on your taxes. He will need to report each sale separately anyhow, so it seems like duplicate work to ask [and pay!] someone else to do this. Since you'll have to dig up the records to provide to the tax preparer anyhow, it will be taken care of then.3) If I buy 100 shares of stock for, say, $1/a share and it doubles, I have... $200 worth. If I sell 50 shares, that means I've taken out only my original investment and what's left is my $100 profit, correct? How does the IRS look at this? Do I have to report the sale? Do they consider the $100 from the 50 shares sold as profit or my initial investment capital??In your scenario, you will have to report that you paid $50 for those 50 shares, and that you made $100 when you sold them. The IRS treats them as individual lots, and you don't get to claim that you are just taking your initial investment out. You will have to pay capital gains on that $50 profit. That's one of the reasons you need to keep good records about all your purchases so that you can report the accurate basis when you finally sell. You may, however, feel like you got your initial investment back and that what's left invested is really profit, but the IRS won't see it like that, so your reporting will be as I've outlined above.