Some thoughts. I started with the intent of restoring to exact originality an RS/SS '67, 350 block, though I did not have the original engine. I found a correct engine for the powerglide, smog car as mine was out of CA. (Car VIN: ~17k, Nov '66; eng VIN: ~32K, Dec 66 - both from LA)
Push rod started to pop off the rocker and wear a bit on the head so I chose to go the roller rocker route, upgraded heads, 2.02 valves, etc...
From my experience I offer the following...
1) I was mindful of the 2-bolt main and showed some concern of building too much power into the engine. Roller cams can equate to higher RPMs. Stronger springs needed, etc... but 2-bolt mains operating above 6,000 rpms is risky business IMHO.
2) Roller rockers would require taller valve covers
3) Consider screw in studs/valve guides
4) For roller cams.... please be mindful of one thing if nothing else... gear at the bottom of the distributor must be changed to the softer brass gear. The factory steel gear will chew that camshaft up.
5) There is also the spacer (actual name is escaping me...) at front of the cam that needs to be installed to keep the cam from walking out of the engine. I pulled my timing cover off and saw the witness marks on the back side of the cover even though I had it installed. I ran the original '67 block for awhile, then...
6) Attached what is sitting in the car now. 383 stroker, 10.5:1, roller rocker/roller cam, 2.02 valves, alum heads, screw in studs/valve guides, dual quad - 2x500cfm.
7) The original SS350 engine is garage art, sitting on an engine stand next to the car.
Anyway... remains fun. Just something else to think about.