I think either engine could get the job done OK. The 360 might need (even more) gear for good towing with tall tires. Neither would win a fuel economy competition.

There would be a lot involved in changing to 360 and less performance. I also would suggest freshen the 440. Loose the DP carb and "big" cam and get a vac secondary carb and RV type cam. If budget allows, set it up with closed chamber heads with quench and decent CR for both power and economy.