I'm one of those guys that takes on the challenge making a stock engine run smooth as silk and count the fan blades during idle. 200 hp is plenty for the way I cruise. The cold mornings that have given me trouble are in the 20's, as I use my car daily unless roads are salted. I suspect my holley carb might be a little lean for a Y block as a Holley rep told me that my carb was a service replacement for a 1960's 289. Thank you for the advice . I did not plug the distributer line when I set the timing but will redo it with the line plugged again. 

I pull the hose at the vacuum can and plug it with a golf tee. Still got those around, but anything will work. Vacuum gauge to full vacuum off the intake.

Since I’m normally working on modified engines, I rarely use factory timing specs. Advance till it pings and back off 2 degrees was my base line.

If you’re running ported vacuum to the distributor, you might try moving to the manifold vacumn carb port, most later holley’s have both. See if that helps on the cold starts.

But it could also be choke adjustment, etc. How cold you talking about?

miker
55 bird, 32 cabrio F code
Kent, WA
Tucson, AZ

Don't quote me, but I think you're right on the gauge reading.  What I used to do on my old '55 Fairlane was advance the timing until it knocked, then dial it back until it doesn't.  Not really scientific but it worked and ran great.  I can't hear anything in my Coupe, so I used a light and just set the total timing.  

This past winter my 56 Victoria was hard starting on some cold mornings. At times, when I let go of the key and the engine didn't fire, the vacuum wipers would sometimes jump a bit. This made me suspect that my timing might be off .  I don't want to rely on the marks on the damper as It has never been reconditioned. I hope someone on this site can advise me on where to plug in my vacuum gauge and which hose to plug if needed. The engine is a 292 with the later model Holley 4 barrel and the 1957 type manifold. The distributer is the 57 and up model. I had planned on using the port on the rear of the manifold to hook my vacuum gauge hose to. I have been using this port to work my original vacuum wipers. The carburator has a small diameter hose that goes to the vacuum advance on the distributer. Should I pull this hose loose and plug it on the carburator end, or should I leave it hooked up at both ends while I set the timing. I assume I will adjust my distributer until I get the highest reading , Appreciate any advice.   George