If I were a dishonest, self-serving crook "owner" of a despicable, morally-bankrupt cesspit of a club, I would skirt around a transfer embargo (using brown envelopes as necessary), bring in players at unsustainable wages, make excuses why I couldn't pay them on time, and see if said mercenaries can miraculously get my club close to promotion. If half way through the season it appears that my club doesn't stand a chance of going up, I'd renege on the wages (as well as paying anything to the idiotic unsecured creditors who voted for my CVA), and let the club (which I detest, but don't tell that to their moronic fans) free fall to oblivion. I'd still hang around and delay winding up long enough to pocket the remaining parachute payments of course, as well as getting 80% of all transfer fees of the players I could sell, and not give a toss about the 500 point penalties the FL will impose for breaking every rule in the book.
All hypothetically, of course.