Depends on so many factors and there's endless options out there. I have the standard weaver up/out davit mounts and davits on my cutwater, with the 260RIB 8.5ft dinghy. I also have the weaver winch attachment built into my cockpit overhang (factory option), although I have no problem lifting the dinghy up freehanded with a rope. I'm also only 41 and 6'4 / 220lbs.
The outboard is another story. It definitely has to be removed unless you have a seawise davit system or weaver lever equivalent that tilts the motor into a vertical position as the dinghy lifts up. I do not have this so I took a different approach. I have a Tohatsu 4 stroke 6hp, and it weighs about 60lbs. While I am capable of lifting it from the motor mount to the dinghy, it scares me in all but the calmest conditions. I am in the process of installing a Garhauer crane on my swim step to handle this task so I don't end up injuring myself or losing my motor in the drink. 🙂 This was the best option for me, as installing a more robust or automated davit system would require removal of the swim step railings and I like them.
There are endless threads on this topic on this forum - I think I even started one recently as I was doing my research.