I wouldn't worry about sealing up your vents, that is not where the water is coming from. The D pillar covers aren't sealed so water will come in from all round them. It really is a wet area and not much you can do to keep any water out.
It's a normal place for rust on the Classics and yours doesn't look very bad at all. It would be a pretty easy fix. You can either take off the back guard, cut out the rust and weld in some repair panels.
Or clean off the rust with a wire brush, pacify the rust with a rust converter as per instructions, paint the area (I like International Paints PA10 primer) and then you can seal up the hole with fiberglass, car bog or knead-it. That will be good for a fair few years and then put it on the to do list if you want to restore it later.
04 L322 Vogue V8 - Work truck
07 Freelander 2 TD4 SE - The wifes
74 Leyland P76 Targa Florio - Aspen Green
91 Kawasaki GPZ900R
Previous LRs = 78IIa series - 81, 93, 95 RRC - D2V8
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