Cooling Issue

For you, I think the only thing left is the anti-cavitation plate that comes on the Hi-flo pumps.And these pumps should be accompanied by a hi-flo stat.
Everything else looks pretty good. Well except I run a 7-blade oem fan.And,I assume you have a stand alone oil-cooler on the tranny. If not, what does she do in neutral? Otherwise you seem to have the bases covered.

Do they make a 17" OEM 7-blade fan? The fan I have is an aftermarket 6-blade 17" piece. I can't run an 18" fan due to the fan shroud I have being from a '67 a-body. I do have a stand alone oil-cooler (B&M stacked plate style). The trans fluid also flows through the radiator though. Should I not have it flow through the radiator?

But this statement has me concerned. Under steady state conditions you shouldn't be seeing the water temp going up and down.The stat just does not work that fast! What I would do is grab an old stat and cut everything off it so that you are left with just the restrictor. Install that and roadtest it.

Thats a good idea.

Without the temperature regulation of those guts, now the temp will run differently with different loads and speeds, but stopped and at idle, with a good fan and pump, the water temp should actually fall.If it doesn't rev it up to 1000 rpm and watch the gauge. If the temp does not fall, either buy or build a hi-flo pump.(The anti-cav plate used to be sold separately). If buying, I have a 16 year old Milodon hi-flo pump,and matching stat, still in action; so of course I recommend them.
My 360 runs 14* idle timing. It has a 276/286/110 cam in it and a 750DP on an AG with unwrapped TTIs. It runs a rock-solid 205*.It idles at 750.I hear the thermostatic clutch kick in occasionally, after a hard run, but mostly it's pretty quiet.And since I like to rev the berries off it, I run an underdrive crank pulley and an overdrive alternator pulley. in an effort to keep the belt on. I have never yet thrown a belt.
I run a restrictor in my bypass hose too. My theory was, that after the stat opens this forces the water to go to the rad. If you notice, the later intakes have a bigger bypass system. I choked mine down to the old size . It seems to work.
Your rad size should be fine. I run a 26" A/C rad from a 73 Swinger 318, in a resized core-support. Yeah it's old, and it is only a 2-row.I guess she's pushing 44 this year. Yours looks all shiny and new. I imagine her calling out to that 340;"common big boy, show me what you got!"

If I buy a new hi-flow thermostat, what temp should I go with? 195? 180?