Self aligning bearings & spherical bearings & spherical roller bearings

I am totally new to ball bearings…

Would a self-aligning bearing help solving the planetary gear / prop shaft mis-alignment / sag and thus reduce vibrations and improve waterproofness ?

Not really. That bearing helps if the shaft comes in at an angle, but not if the shaft comes in at the wrong position. (X-Y coordinates) If the shaft is only out of position by 0.5mm, that can cause binding. There should really always be a flexible coupling between two shafts.

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Thank you @MaxMaker . What about spherical bearings ?

SKF Explorer sealed spherical roller bearings are designed to withstand high loads, misalignment, poor lubrication, contaminants, moisture and more.

Spherical is the same thing as what you posted at first. They only work when a shaft is at an angle. Whenever shafts allign, even precision machined ones, they will look like the first figure. Bearings have very very little radial play, so you need flexible couplings.

Figure 3 is the application for your bearings. (Different Y coordinates)