The basic answer to your question is No. TurboTax will not handle all of the things you listed. It will not do what you want.
TurboTax is not designed for traders or for high volume trading. It does not analyze your trades and identify wash sales. You have to tell TurboTax if a particular sale is a wash sale.
You enter only sales into TurboTax, not purchases. And you do not enter transactions in an IRA at all, since transactions in an IRA are not reported on your tax return.
