I kayak all the time from my boat and find that it is easiest to enter and exit the kayak from amidships at the lifeline gate where there are two strong reinforced stanchions to hold on to. I recently added one of those rubber fenders that is also a step that tie's to the two stanchions. With this method you are holding both stanchions while you slide over the side with your stomach facing the hull of the sailboat. The key is to step into the center of the kayak while your other knee knee is on the rubber step. You are holding onto the stanchions the whole time until the end where you have to let go and drop into the kayak seat. When you exit the kayak everything is done in reverse. This is much easier than from the stern as the boat may be bobbing up and down with the waves and it can be dangerous or even a deadly maneuver. The guests on my boat who don't regularly kayak have no problem with this technique. I am also in the northwest and don't want to get wet.
I agree with this method completely. If the water is flat it almost doesn’t matter. But with any wave action the boat and the kayak are not in harmony if boarding from the stern. The step addition is excellent. It tethers onto the bottom eyes of the gate.
I found kayaks aboard my triaman to be far easier to work with. I only hire someone to take me to the vessel when transporting very heavy items. One person and four 22 litre gerri cans is no problem.
Never buy a phone for more than $100 usd. Over 10 years living aboard using kayaks I lost two nice phones before learning that inexperienced crew dump the kayak even in calm waters.