Mild 360 engine rebuild recommendations

360 heads are open chambers. You cannot get any Squish/Quench out of that combination, with flat tops; which means, that the engine will be somewhat pressure limited, to prevent detonation.
False
Pressure makes heat, makes torque, which, times rpm, equals power.
IE, lack of pressure is lack of power; especially at lower rpms.
To "get some bottom end back", you will need;
A) a higher stall convertor, so the engine doesn't have to operate in the marshmallow zone, and
Only if the camshaft is too large for the stall converter and gear set/tire combined. The last factor is weight of the car.
B) higher ratio rear gears, so the engine can spool up into the power zone and sorta hover in the powerband, after the shifts.
Neither of those are cheap.
Agree-ish
C) IMHO, if you want to keep those heads, you'll need to get some specialty-pistons with machinable Q-pads, cuz without Quench,typically yur engine pressure will be limited due to detonation.
False X‘S 2. Small done pistons are readily available.
He doesn’t NEED to go there. The KB-107’s machined to a zero deck height and proper head gasket can net a 9.8-1 ratio.
Here's the deal;
Early 340s were rated at 10.5Scr.
They weren't that.
At best maybe 9.8, and they had forged pistons/forged cranks, and a pressure bleeding camshaft, which all worked together to try to prevent detonation, even with best leaded gasoline of the day.
Disagree. The camshaft was at a wide 114 LSA.
If you copy that deal with; hypers, a cast crank, a tight LSA street-cam, and todays gas ............. you could be in for a world of hurt.
Disagree. But I’d rather run 87 than 93 for an easy and possible everyday driver.
Yur plan is pretty good, but I'll never run open chambers again. And if you machine yours, you always take a chance that the machine shop will get all the angles right. I would trim some fat off your parts list and go straight for some closed chamber heads, and since I have had such a great experience with alloys at up to 195psi/still on 87E10 pump gas, how can I not recommend them...........

I also have a set of standard 360 heads that have had he valves done, would I be better off with them?
Use the best set. If the 2.02’s are the better set, use them. I’d like to say moving the 2.02’s to the smaller 1.88 valve head is good but now it’s a cost issue. This is up to you and I don’t see the worth unless the 2.02 heads are shot out and garbage.