So I was wrong about the restart of the holding period upon CONversion of CONvertible preferred shares. One can tack back to the date of issuance of the original CONvertible preferred shares.
Yes. The only date that matters is the date you paid for the securities.
So an issuer acquiring an crony's biz entity is NOTT a way to 'pay for it with free-trading shares'. Instead, if payment is made in shares nott covered under an effective reg statement, whatever shares are paid to the selling party are restricted - with~OUTT regard to whether they are common of CONvertible preferred series.
No, because an issuer can't just issue unrestricted stock whenever it wants to. That would make it way too easy. Such an arrangement would, in fact, be quite unusual. Penny stock shells normally change hands through the sale of a control block. The control block is usually preferred stock. It may or may not be convertible; some supervoting preferred isn't.
It doesn't really matter, because if the new owner wants to raise money, as soon as he's in control, he can sell (restricted) stock in private placements, or, if the company is an SEC registrant, in S-1 offerings.