OK, so I am in the process of building a 408 W2 based stroker. I'll give you the AS_IS & FUTURE configuration and some justification for what I have picked.

The car is my 1980 Dodge Diplomat Coupe, 3600 lbs (race weight), 4K stall converter, 4.10 SG gearing, the same intended use split as what you have.

1) AS-IS (current combination)
360, 0.020" over, factory heavily ported heads (2.02/1.60 - 291cfm@0.550" Intake, 177cfm@0.550" Exhaust), 10.5:1 static CR, hydraulic flat tappet cam: HE3844AL (Hughes Engines) - 238/244@0.050", .535/.540 lift @ 108 LSA, Performer RPM intake, 1-5/8 primary tube headers (Hooker) into 3" X-pipe exhaust system

2) FUTURE
408, 0.030" over, MP W2 Econo long valve heads (2.02/1.60 - 252cmf@.600" Intake, 200cmf@0.600" Exhaust, stock out-of-the-box numbers, these heads have not been touched yet, they will be ported next), 10.5:1 static CR, hydraulic roller flat tappet cam: XR292HR custom grind (112 LSA vs 110 of catalog cam) - 240/248@0.050", .584/.581 list @ 112 LSA, higher lift due to the 1.6 ratio rocker arms), Edlebrock 2920 Victor W2 (single plane), 1-7/8" primary tube headers (TTI) into 3" X-pipe exhaust system

Alright, so the big driver here was the move to a W2 setup in combination with hydraulic roller cam. Since my intended use is 95% street I picked up the XR292HR cam but ground on 112 LSA to give me slightly better street behaviour. Most of the feedback I got here on that choice was that I am giving up power and something like 108 LSA would be a better choice. Given that I am going from a Performer RPM (dual plane) intake to a fairly stout single plane I figured it made sense to do a 112 LSA.

I already have a nice 4K stall converter. Previously I was running a 2800 and with my HE3844AL cam that simply wasn't enough, the car was slow to pick up. Moving to the 4K stall was literaly a day&night type of a change, this put the combination right into the "sweet spot", or at least that's my perception. Originally I was running a 3.91 gear, then moved to 4.10 a couple of years ago. This was not a significant change, but the ol' "butt meter" did certainly register. Seemed like a move in the right direction because the overall combo felt like it finally came together.

Now, moving to a 408 stroker I figured I could take a chance on a dual to single-plane intake switch. The 112 LSA should support that further given that I need to run power brakes as well and currently pull about 7-8" of vacum @ 800 RPM with the HE3844AL cam, so brakes are alright at that level, no issues, but I am using a dual-tandem brake booster (which helps).

Given what you have, 2800 converter and 3.55-3.73 gearing, I would say stay below the 234@0.050" cam duration. If at all possible go roller route since that just makes sense given the on-going zinc/oil-mix changes. Lunati seems to have some pretty nice cams, something like the Voodo Retro-Fit #20200712 (60412), 2200 - 6200 RPM range, .535"/.550" lift with 231/239@0.050" and 282/290 advertised on 110/106 LSA/ICL. Their catalog description reads:

"High performance street cam. Likes up-graded intake, carb and exhaust. Needs 2800 RPM stall converter in most cases. Requires 9.5:1 compression."

Here is another one from Herbert Cams, I love the lift on these and will probably go that route if I end up not liking the XR292HR cam: CEH3, 2200-6000 RPM range, .525/.525 lift with 225/225 @0.050" duration on 110 LSA. Their catalog description reads:

"Intendedfor street/strip applications. 2500+ stall or manualRecommended."

They show some interesting grinds right HERE, but the pros on our site here can better interpret the suitability of the options than I...LOL!

I probably would not go much bigger than that though.