First thing, just because I do it doesn't mean anyone else should. Your risk tolerance may vary.
100 miles referred to round trip distance, 40 miles off shore plus a bunch of trolling. Furthest out I've gone is 55 miles.
It's fine, further just takes longer, more fuel etc. There are interesting birds and some times unique whales to be seen. Saw a huge leatherback turtle off Brooks one trip. I'm very cautious about weather conditions. I only go on really nice days.
Safety gear: Dry suit worn the whole time (exposure/hypothermia is a serious risk), PLB in the pocket, foam life jacket not an inflatable, handheld VHF, fixed mount VHF, Class B+ AIS transceiver, two chart plotters, fixed and hand held compass, I tie off to the leaning post with a short enough rope to not go past the transom when fishing.
I'm usually alone in the boat, but have gone out with one friend who works on the west coast in small boats professionally. I have not gone out with a buddy boat.
I agree, everything else being equal, a bigger boat is probably safer. A buddy boat is a very good idea and definitely safer than going alone. Twin engines, also safer. Knowing your boat, how to fix things, having common spares, tools and materials is a good idea. The boat I use is self bailing and foam filled so won't sink, but could still capsize. Might be able to swamp it in the right conditions as well, but it does have a pretty low transom to let water out provided you can power up and lift the bow. Fuel, I carry 85 gallons, so burn a half tank or less. Tons of reserve. I rely on the kicker in case the main dies. I suspect it would be a very very bad scene even with the kicker if the weather picked up at the same time. Some things like a failed alternator are covered by running two very large batteries. Boat will run for a full day on batteries alone. Make sure your equipment is in good condition. I put all new power and systems in my boat to improve it's reliability. Take extra food and water in case you get stuck out there.
Couple philosophical points. The difference between what is possible and what people are comfortable with can be huge. Before getting the whaler I ran around the west coast in a 14' soft bottom zodiac with a 20 horse on it. Biggest trip in that thing was over 600km in 10 days up and down the west side of the Charlottes from Tasu to Port Louise. Plenty of people run all over the coast in 12' aluminum boats with 9.9's. I had friends that used to go to Rose Harbour from Queen Charlotte in one. I know of one guy that went from Bowen to Queen Charlotte in one. There's a lot of talk about whether something is safe or not. From my perspective that's an inaccurate way of seeing the world. Many things are very unsafe, but nothing is absolutely safe. There's always risk, it's a matter of how much and whether a person cares about it. I worked with a guy that almost choked to death on a lamb chop eating dinner by himself at home. He had to heimlich himself on the corner of the kitchen counter. He totally, 100% could not breathe. He for sure would have died had he not thrown himself against the counter. For me it's about being prepared, knowing what you are comfortable with and try not to put others into situations they aren't comfortable or prepared for.