Starting with the points, a matchbook or feeler gauge set to .017 thousands is only good enough to get you in the ballpark. To really dial things in, you need to hook up a dwell meter. The spec dwell angle for an IH v8 is between 28 and 32 degrees with 30 being optimum. If the dizz cap and rotor look sketchy, that's going to effect performance. Same with spark plugs and plug wires. Those are basic tune up items.
A Holley 2300 in proper state of tune is tough to beat when it comes to two barrel carbs for these engines. The older style like you have is roughly 300 cfm, but don't get caught up in that number too much. Its certainly big enough for your 345. Going to a 4bbl isn't going to give you all that much more performance-wise than what you can get out of your current carb. The best way to set your idle mixture screws is to turn them all the way in until lightly seated, then back them out an equal 2 turns. This is your starting point. Bring the engine up to operating temp. With a vacuum gauge connected to manifold vacuum, slowly turn one screw in until the needle peaks. Do the same for the other screw. At a curb idle of @ 750 rpms you want to see a steady reading on the vacuum gauge between 18 and 22 hg.
These engines were never intended to be jaw-dropping performers. They were over-engineered from a durability and longevity standpoint, but they don't breathe worth crap. The valves start floating at around 4 grand, so they're not high-winding mouse motors. These are truck engines meant to move heavy payloads slow and steady, while running at their maximum recommended rpm rating all day long, day after day.
In a light line vehicle such as a Scout, one should expect a level of performance comparable to a stock Bronco/blazer/ramcharger/wagoneer of the same era. None of those rigs set any land speed records. Don't expect your Scout to either.
I don't know how stringent the deq inspection is in portland, but before I lost too much sleep about where the timing was set, I might be more worried about the fact that my carb isn't oe. That's going to be easier for an inspector to notice than where your ignition timing is set. I doubt the dolts even know to time an IH v8 off the #8 cylinder!
