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Greetings, Sam, and welcome.

<<Schwab tells us that we need to liquidate the stock, deposit the money into the IRA, then repurchase the stock. This would mean paying commissions of $90 which seems a little dumb.. Is there any reason one can't simply deposit equities into the Roth IRA, using their current price as the "dollar value" (for use in calculating the $2000 contributed)?>>

Schwab is correct. The tax code won't permit the deposit of securities to an IRA. The only exception to that is if the securities are part of a rollover from another IRA or from an employer's qualified retirement plan. Normal annual deposits must be made in cash only.

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