Rogue / Fighter or Fighter / Rogue + Additional Help

[Deox]

Possibility of a new character being introduced and was looking for some feedback. As the title, need help in deciding to start rogue and then go into fighter, or start fighter and go into rogue.

The core concept would be a Rogue (Mastermind) 4 / Fighter (Battle Master) 6; using his abilities to "help" from range, while still mixing it up in melee with a whip. Sentinel would also come into play.

Stats are still up in the air, but my first thoughts would be:
STR: 8, DEX: 20 (after race / ASIs), CON: 14, INT: 10, WIS: 10, CHA: 16. Feats would be Inspiring Leader and Sentinel. Not sure on Fighting Style either, perhaps Dueling?

Additionally, the maneuvers I was first leaning towards were: Disarming Attack (drop weapon with whip and use item interaction to "return" it to me), Rally (personally just like the fluff, combining with Inspiring Leader for mini-heals), and Commander's Strike.

Any thoughts on if this concept is even worth going after? If so, what recommendations would you make? Magic items suggestions as well? Thanks!

[Waifu]

First, decide whether you want to start with Fighter or Rogue. Going Rogue first will get you more skill proficiencies, but Fighter first will get you heavy armor proficiency, which will alow you to get your AC up to 18 if you don't want to spend a feat on Medium Armor Master and don't mind the disadvantage on stealth.
Also, the temp. HP from Rally and Inspiring Leader won't stack. I'm not saying don't take it, but keep that in mind.
Since it looks like you're going for more of a support role, maybe consider either taking the Magic Initiate feat or a level in Wizard to take Find Familiar, and get some nifty cantrips as well. Your familiar will also be able to take the help action, which means you can help two allies at once.
As for fighting style, I would recommend Defense or Dueling, as they give you a flat bonus to defense or offense.

[Crgaston]

With a strength of 8, heavy armor will be useless. Studded leather and 20 Dex is 17 ac. Good enough, especially since you’ll be able to grab a shield if necessary. Your main choices are 1 more skill and Dex/Int saves vs a couple more HP and Str/Con saves.

I’d go Fighter for the Con save if you can pick up the skills you want from race and background. You’ll have a good Dex score to mitigate lack of proficiency in Dex saves, and then Rogue 7 (if you get that high) gives you Evasion, so...

[Deox]

Thanks for input; all sorted!

[2D8HP]

Besides the extra armor and weapons proficiencies, going Fighter first gets you proficiency with Shields at first level, which helps your AC considerably.

Going Rogue first nets you one extra skill than if you went Fighter first.

I usually find that I prefer having PC' s that went Fighter first, but I like playing a first level Rogue more than I like playing a first level Fighter (unless of course the lack of a shield means my PC didn't survive).

However you get there, a Fighter 6/Rogue 4 is a fun combo.

[Deox]

Besides the extra armor and weapons proficiencies, going Fighter first gets you proficiency with Shields at first level, which helps your AC considerably.

Going Rogue first nets you one extra skill than if you went Fighter first.

I usually find that I prefer having PC' s that went Fighter first, but I like playing a first level Rogue more than I like playing a first level Fighter (unless of course the lack of a shield means my PC didn't survive).

However you get there, a Fighter 6/Rogue 4 is a fun combo.

I had a similar train of thought. As far as the character, yes the Fighter / Rogue is a great combination. I love having so many choices for Bonus Actions (Cunning Action, ranged "Help", Commander's Strike, Rally) depending on the situation. Played the first session as this character and was really fun.

Now to inspect every nook and cranny in each scenario to see what I can whip / grapple onto and swing around like a mad-man.