Howdy Teppo and All:
I'm sure enjoying your saga. You've got some more good suggestions to follow up on. As Tony said- be sure to verify pump pressure 1st.
Given your vacuum readings, I'd be inclined to use a 5.5 PV. Also verify the size of the fuel orifaces to the PV channels. Have you checked vacuum readings after altering the initial timing?
Also the transition from idle to acceleration to cruise seems to be the problem areas. That causes me to think that the solution will be a combination like a richer low speed idle air screw setting, a lower PV number, the correct main jet and float setting.
The heartache of the 2100 is lack of availability of jets, a less refined idle circuitry and PV, but I don't see why the mixed pair of main jets won't work. The log plenum should help to even out to A/F mixture. Watch for fuel distribution mismatches by reading your plugs.
Tuning a 2100 is very similar to a 2300. The difference is more tuning options and availability of parts with a Holley- which are more specific and exact. Setting the float, for example, is as easy as loosening a set nut and turning a screw- no disassembly at all. Tuneability of the Holley is a big plus!
With the performance advantage of the 2300 over a 1.14, plus the tuneability, I'm wondering why you haven't gone to the Holley already. About the only advantage of the 2100, in your case, might be the annular discharge venturi booster, which improve fuel atomization and distribution.
Adios, David