The character I feel I can't update, interestingly, is my primary Living Greyhawk character, Kerrick of Nyrond. He was a human arcane trickster. Arcane trickster is one of the options given for rogues; but now, their spell progression has slowed dramatically. Kerrick was a typical rogue for his early levels, then somewhat underpowered for four levels as he did his multiclassing. Then he got third-level spells, including Fly, and it all came together. Once he reached 10th level, he became quite the monster, courtesy of the suite of Orb spells and Improved Invisibility.

I can make an arcane trickster, but I can't make that arcane trickster.

On the other side of the coin, I think ranged rogues are now much more viable. You no longer need to be flanking or invisible to sneak attack reliably.

Yeah, I wonder why a rogue would ever want to melee in the new rules. I mean, I guess you could two-weapon fight to get two chances at landing your sneak attack, but you're better off keeping your squishy self at a distance.

I vaguely remember wood elves getting a Strength bonus, now.

Yeah, converting characters is a little rough, though at least it's easier going from 1e/2e/3e into 5e than it was from any edition into 4e. (It's telling when WotC had a 1e/2e to 3rd character conversion guide on their website from day 1, but for 4e it took them months and then it was basically "Yeah, just rebuild your character from scratch.")

At some point, I may muck around with trying to convert Kelrick, my Fighter/Rogue/Sorcerer/Paladin (who I still thought of as a Rogue) since I converted him from 2nd Ed (where he was a dual-classed Fighter/Thief) to Skills and Powers (where he picked up a smattering of magical know-how) to 3rd Ed.

Human Noble background Rogue is as far as I've thought about it. Probably will be Thief archetype, as Arcane Trickster is too much magical oomph for him (he only had a single level of Sorcerer to replicate the minor magical powers he had from Skills and Powers). Probably take the feat that gives you some minor magic in 5E rather than bothering with multi-classing. Not sure if Fighter is worth it. Getting the Fighting Style might be nice, but the weapon and armor proficiencies don't amount to much since the Rogue is already proficient with anything they can sneak attack with anyway and sticking with it for the extra crit range from Champion seems like it would delay your sneak attack dice too much.

As much as I groused about it before, the Oath of Vengeance Paladin would fit the secret division of his family's Paladin order that Kelrick ended up joining at the end of his career. Though that's another 3 levels before it even becomes relevant.

Huh. I've been looking through my various character notes for previous editions. In 4e I had apparently planned at one point to create a minotaur warlord/barbarian called the Kowgan.

Interesting. I was thinking the bastard sword was also called the hand-and-a-half. I googled that term and all the top results were for longsword. Can you tell I have wielded a lot of bastard swords? It's like my world has turned upside down!

The fun thing with medieval weaponry is the people actually using the weapons didn't really differentiate in exacting detail between them. They generally used basic terms like "sword" or "mace" or darkly humerous slang like "holy water sprinkler". Modern scholars have to make up their own terms so they can communicate with each other. (Such as the Oakeshott Sword Types).

Actual two-handed swords meant for battle (rather than parades) are also a lot smaller than one would think based on fantasy artwork.

Granted, I didn't really know much about any of this stuff until I took a class on Medieval Italian Longsword fighting from a local historical fencing society years ago and started looking into the sources they referenced.

So I ended up converting Kelric to 5E. Rogue 11/Fighter 2/Sorcerer 1/"Paladin" 1 with the Spring Attack chain and a homebrew Luck feat became Human Noble Rogue(Thief) 11/Fighter(Eldritch Knight)4 with the Mobile, Lucky and Skilled feats.

Eldritch Knight was a little kludgey, because none of Kelric's meager magical powers were blasty in nature, but I stuck with Abjuration spells and took Detect Magic as my one free choice. (I don't understand why this isn't a cantrip in 5E. It worked fine as such in 3.x and Pathfinder, even with the latter's infinite cantrips per day.)

On a related note (though I didn't use it for Kelric) somebody put together a web-based 5E character generator. [link] It's a little clunky, but it works.

Had a game night with strangers, a Meetup event. We played Cards Against Humanity. We had a 5 way tie going into the last card. Miracle of Miracles, my remaining card worked wonderfully with the black card, and I won the night.

I haven't played Cards Against Humanity but it sounds like a blast.

It's better with folks you know. Last night was fun, but not knowing how these people think, it was a lot harder to pick cards. And it's a game where you need to know things. Lots of random things. One of the players won with the 3/5ths provision, and didn't know what it was. So a few of us pointed out some of our sadder constitutional history.

Someone has some GotG-inspired fun with the new game Destiny: [link]