So... basic question... I'm thinking about making an Anchor 2H Weapon build that focuses on slapping people around with a giant Ship Anchor. Does the Rough and Ready trait with 1 rank in Profession: Sailor give the bonus for an Anchor?
Yep.
Personally, I feel like Catch Off-Guard+Surprise Weapon is better for a improvised weapon fighter (due to the trait essentially taking the place of Weapon Focus+Greater Weapon Focus in bonuses, because you can't take those anyway), and opens you up for Improvised Weapon Mastery.
Hm... hadn't seen Surprize Weapon, kinda wish the two of them stacked now to be perfectly honest.
Are there any other good Improvised goodies I should be on the lookout for? Improvised Defense looks fun, but lossing the benefit when you attack is really icky...
Not particularly. A lot of stuff requires proficiency, and it is HOTLY debated as to whether feats like Catch Off-Guard grant proficiency in the first place. (feats that specifically grant proficiency also have similar language to Catch Off-Guard [Simple Weapon Proficiency], so you can see where the debate part comes in. This is a can of worms not worth opening, trust me. Last time this train of thought came up I believe it was concluded that nobody has proficiency ever RAW. Hyper-literal interpretations are where the rules truly break down entirely)
Equipment Trick gives some cool stuff but there isn't anything for an Anchor specifically. Anvils, however, get some great stuff if you are interested in fighting with a 100lbs brick of solid metal.
And last but not least, who even knows if you can make a masterwork improvised weapon, let alone a magical one. It's very DM reliant. I'd say just let your DM know that in the rules, improvised weapons are basically anyone's game and a fairly liberal reading(and probably intended reading given the dev's insistance that the rules are written in plain English and not legalise) doesn't otherwise make them stronger than any other fighting style, but a hyper-restrictive one makes them useless and puts holes in the boat of the whole system.
I always thought something like a Magus would make a good improvised weapon character since they can enchant their weapons on the fly, and thus ignore the "must be masterwork" stuff that people talk about (Or any of the other classes that can do that, but Magus seems the most obvious).
Or if the weapon enchants are the only part of Magus that you care about you could go VMC Magus on some other class (probably better actually since you could go full BAB to get Improvised Weapon Mastery earlier).
Also my Pathfinder-Fu isn't good enough for this, but are there any traits/feats/etc that give you bonus when using a "Piercing/Slashing/Bludgeoning weapon" or something like that? Coz if there are you could try some of those to improve your improvised weapon fun ...?
The cad fighter archetype and makeshift scrapper rogue archetype can combine to make a heck of an improvised weapon user that can debuff a foe into next week with dirty tricks while still dealing some damage, too. The build is discussed here if you want to check it out - the page is much better at detailing it than I am. :) It doesn't come fully into its own until level 7 or so, but it's a fun way to make a martial into a more support-type character.