A good question is what else does your organization do in-house. You're a logistics company. That probably means you have some trucks around. Who maintains thos

A good question is what else does your organization do in-house. You're a logistics company. That probably means you have some trucks around. Who maintains those? And how well? If the organization can manage its own maintenance operations without crises, it can probably manage software maintenance. The tradeoffs between maintenance expenditures, downtime, and failures on the road will be understood and accounted for properly. If almost all the trucks are out working and the maintenance staff is doing oil changes and replacing worn fan belts, you're good. If you have six trucks out back with parts missing and one being towed in by a wrecker, while the guys in the shop are trying to fix a truck by cannibalizing one of the dead ones, developing software you have to maintain probably won't end well.