As Jim Harman said, always use the exact number of shares traded and the dollar amount (+/- any commissions). Let Quicken calculate the price per share to as many decimal places as it wants to. Any other way you'll end up with differences in the total transaction dollar amount or, worse, an incorrect number of shares traded. Either way, your account register won't reconcile to the actual holdings and cash balance.Use the information provided on your brokerage statement or the website to get the correct numbers.
So, for#2 enter exact number of shares and exact total dollar amount, e.g. 0.123 shares, $1.99
#3 enter a Miscellaneous Expense transaction instead of a Cash Withdraw. Categorize it to, e.g., Investment Management Fees. $1.99
#4 Buy transaction for the paycheck contribution: Again enter exact number of shares bought and total dollar amount, e.g. 14.045 shares, $234.56
The paycheck deposit transaction in your checking account should have a transfer to the investment account: $234.56
The net effect on the investment account's Cash Balance after these 4 transactions should be $0.00