Re: dayshapes for towed dinghy?
Never seen or heard of the USCG citing recreational boaters for towing any other recreational boat without dayshapes, let alone a dinghy. Have watched for years folks get towed in after running out of gas, and of course many sailboats with dinghies, going right past the USCG station. We're on inland waters so maybe the regs are different, or just not enforced.
That is a big dink for your boat -- more than half your length!