Learn how to do a two-boat rescue. Learn how to do a connected tow. Be prepared to raft-and-run if conditions get bad fast. Hopefully there is land down-wind, maybe not where you want to be but dry. Not many drown on dry land.http://www.kask.org.nz/rescues-how-to/
The two-boat rescue can be practised on land. Note kayaks can face either way (same way or opposite ways) despite what some say. Rescuer put their weight on the fore deck of the kayak being rescued while the swimmer is getting in. Weight for stability and easier to hold on. The rescued kayak can accidentally be capsized away or towards you while someone is getting in.
Kayaks - my partner's 5.2 metre x 62 cm beam, mine 5.02 metre x 510 cm beam. Yes we use rudders. Yes we build our own. Yes we are a few decades older (3+).
Kayak in the window - make a clip-on roller to fit on the window-sill. Make life easy.
At 44 years old you are just a kid so a lot to learn yet.