Alright so this is my build I have in mind for my Cowboy. I'm trying to create a hardcoe survivalist crit chance build and will probably use the medicine stick as my all around gun. This is the perk path I have

Level 2- Confirmed Bachelor
Level 4- Educated
Level 6- Light Touch
Level 8- Travel Light
Level 10- Finesse
Level 12- Cannibalism
Level 14- Bloody Mess
Level 16- Better Criticals
Level 18- Cowboy
Level 20- Grim Reaper Sprint
Level 22- Action Boy
Level 24- Action Boy
Level 26- Nerves of Steel
Level 28- Pack Rat
Level 30- Hand Loader
Level 32- Silent Running
Level 34- Sniper
Level 36- Jury Rigging
Level 38- Grunt
Level 40 - Tunnel Runner
Level 42- Toughness
Level 44- Toughness
Level 46- Gun Slinger
Level 48- Long Haul
Level 50- Just Lucky I’m Alive

But it just doesn't "Feel quite right." I don't know why but it feels like it can be better optimized. I'm not trying to hardcoe min/max because I am trying to stick to a theme (like having gunslinger) but I feel even the placement on the levels could be a bit better. Anyone have any suggestions?

I'm pretty sure you're doing a crit build. What is your starting SPECIAL? Did you factor in your Agility and Luck (which are most important, IMO... seconded by Endurance) pre-implants to max them out to 10? Otherwise you would need to have some perk points in Intense Training. And just as a heads up, some of the REALLY fun Guns like the AMR requires 8 Strength. And at some point, you might find yourself wanting to switch your light load out and put on Power Armor and use Miniguns or LMGs instead (I've been there), so you might think to factor that in as well.

I find a 5 Strength to start is decent. 1 point with implants, 2 with OWB completed, another one with LR completed. Came out to 9, put on Power Armor and you're good to go! I like to start with 9 Agility and 9 Luck for such build as well. You can scale down on Intelligence (5 would be OK) because you're not spreading out too much. I would just set Charisma to 1 because what's the use, right?

And this is just for fun: I find that having Chemist (double chems duration) and completing Aba Yaga Honeymoon to get the Turbo recipe can be useful for REALLY bad close-quarter situations when you need to charge in/backpedaling while guns blazing (Think... multiple Deathclaws at close quarter. RAWR!!). Also, double Stealth Boys duration is always fun. There are also two Implants GRX perks you can get, but real Turbos works better, but just FYI.

I can understand your choice on picking Grunt, just as back up because Medicine Stick is not always reliable. But think of it this way: Grunt increase massive damage for grenades AND grenade launchers, while Cowboy increase damage for Dynamites. I would have gone with an Explosive build as well. And with Honest Hearts, you can make unlimited Nuka Cola, and with Nuclear Chemist you can make unlimited Nuka Grenades!

And lastly, I think you can do without these perks: Confirmed Bachelor and Jury Rigging. Honestly, by the time you're level 25, if you were a diligent scavenger you would be able to make TONS of Weapon Repair Kits, so Jury Rigging is totally a waste. And Medicine Stick is usually WAY overkill, so IMO picking CB is also a waste.

Thanks! I think you've given me some more ideas. Anyway my starting special is 5 6 7 1 4 8 9. Also you got a good point about also having an explosives build. I didn't think about that. Oh, also this is my second playthrough.