You would not need to roll over every month though. Look at the daily trading volume for CL @ CME: longer term traders are using the June and December contracts. This means that you would only need to roll over twice per year.Isn't it possible to trade a perpetual/continues contract?
Is it only possible to trade the monthly expiries?
https://www.cmegroup.com/markets/energy/crude-oil/light-sweet-crude.quotes.html