Schiff is like the Jim Jones of money management. Thank God they guy has stayed away from Bitcoin. When he jumps on board I would take it as a sign that it's time to bail.
I remember him screaming for people to buy gold when it was dropping from 1800,1700, 1600 etc. He called for $5000 to $10,000 per oz in few years.
I don't remember him saying anything about it when it was around $300.
Now, his Overstock argument is one sided. He assumes that people who already have bitcoins will go on Overstock to spend it. Effectively selling their coins.
IMHO, the retail acceptance is positive for bitcoin in terms of broader acceptance and an overall image. The actual mechanics of bitcoin retail transactions should have no effect on the price of bitcoin. If you want to buy something on Overstock with bitcoins, you have to buy bitcoins and spend them on Overstock site (they would sell bitcoins using bitpay).
He might be right about one thing, the price of bitcoin cannot go up without new buyers coming in, but that is kinda obvious.
On the last drop, about 1M exchanged hands (if you add up volumes all the exchanges). Assuming (I don't remember where I read it) that 3M are in inactive/lost wallets, that still leaves a large number of whales who did not participate in this drop.
So price pressures might still continue for a long time. Looks like FBI has not dumped their holdings, if they do, expect the price to drop to <$50 because there is no liquidity to handle 100,000+ BTC type of trades. I don't expect FBI to be picky about the price they get for their coins. After all, it is not their own money.