Open Palm Monk/Investigative Rogue Multiclass

[RSZealot]

Recently, our group's former DM expressed the desire to run another 5E campaign, and we all had a session zero to make our characters. I decided to make a Wood Elf Monk with the criminal background. The idea is that he was a upper mid-level mob boss who joined a monk monastery to seek atonement for his past misdeeds. Over the course of the game, I want the stakes of the campaign to push him to going back to his old ways; i.e. multiclassing into Rogue. Specifically Inquisitive to take advantage of the character's focus on Insight (story-wise, he's a bit of a walking lie detector).

I was planning on going Monk 17/Rogue 3, but I might go Rogue 4 to pick up another ASI or Feat. My first thought was to immediately go into rogue at level two to establish his background so to speak regarding Thieves' Cant and Expertise.

The problem is that I'm fairly new to multiclassing and I would love some help with which levels to take which class, feats vs. ASI and such.
The characters stats at first level are 10 17 12 14 16 13.

[Sans.]

Wood Elf is a good race, and for stats I'd swap Int for Con but the rest is good. Just start Rogue; Int is only slightly worse as a saving throw than Str and you'll pick them all up eventually anyway if your campaign gets to that point, plus the extra skill is nice. Empty Body is amazing if the campaign gets to that point, but if not Rogue 3 is decent. Sneak Attack doesn't work with fists, however. You could take the second Rogue level at 6 after Extra Attack or after any of the ASIs; same with the potential third.

[RSZealot]

Wood Elf is a good race, and for stats I'd swap Int for Con but the rest is good. Just start Rogue; Int is only slightly worse as a saving throw than Str and you'll pick them all up eventually anyway if your campaign gets to that point, plus the extra skill is nice. Empty Body is amazing if the campaign gets to that point, but if not Rogue 3 is decent. Sneak Attack doesn't work with fists, however. You could take the second Rogue level at 6 after Extra Attack or after any of the ASIs; same with the potential third.

Well, the character kinda has to start as monk for story reasons regarding the party's first meeting. The DM mentioned he expected the campaign to take us to "somewhere in the 10 to 15 range", but then his first campaign he said would take us to around level 20, and I ended up as the highest leveled at nine.

He did however agree to letting SA's work with fists since a monk's unarmed attacks have the same traits as a finesse weapon.

[Mortis_Elrod]

What level are you starting at ? Normally I would say rush monk to 5 for extra attack and stunning stike but since he gave suck a good boon, I would go monk 2 rogue 3 and decide from there. This gets you the rogue background, with the bit of monk training. Makes sense to me anyways that you'd be more experienced as a rogue than a monk, though I wouldn't go farther than level 4, and probably not that if it's a short campaign.

This is of course you start level 5,

For progression from 1 I would do

Monk 1
Monk 1 / Rogue 1
Monk 1 / Rogue 2
Monk 1 / Rogue 3
Monk 2 / Rogue 3
Monk after that. If you get to 15th level.
Monk 12/ Rogue 3. Extra monk level over rogue for Ki Point. Only difference really. If 10th level is the end and you know it.
Monk 7/ Rogue 3. Stillness of Mind and Evasion are worth more than extra ask I think. Though if 20s in Dex and Wis are more important than I can't fault you.

[RSZealot]

What level are you starting at ? Normally I would say rush monk to 5 for extra attack and stunning stike but since he gave suck a good boon, I would go monk 2 rogue 3 and decide from there. This gets you the rogue background, with the bit of monk training. Makes sense to me anyways that you'd be more experienced as a rogue than a monk, though I wouldn't go farther than level 4, and probably not that if it's a short campaign.

This is of course you start level 5,

For progression from 1 I would do

Monk 1
Monk 1 / Rogue 1
Monk 1 / Rogue 2
Monk 1 / Rogue 3
Monk 2 / Rogue 3
Monk after that. If you get to 15th level.
Monk 12/ Rogue 3. Extra monk level over rogue for Ki Point. Only difference really. If 10th level is the end and you know it.
Monk 7/ Rogue 3. Stillness of Mind and Evasion are worth more than extra ask I think. Though if 20s in Dex and Wis are more important than I can't fault you.

We start at level 1, and I like the progression path you suggested. For some reason I hadn't even thought about rushing to Rogue 3, but it would make the most sense given his past. Thanks.