Racking is allocated at the Commodore's discretion on the basis of "use it or lose it". In an utopian display of equity, frequent sailors and contributors to club life get priority, newbies start in, and less frequent sailors get moved to, the penthouses. Non-sailors get evicted.
Although it's a little bit "chicken and the egg", Wednesday twilight sailing counts towards the frequency assessment because no frequent sailors want to regularly lift boats up/down from the ceiling. If you come down to sail, your boat will come down in the racks to meet you.
PS: money probably won't buy you a better rack, but you won't know for sure unless you try your luck.... send a donation via DBSC's tax deductible ASF fund.