Looking for advice/insight on car

Even if you put a 440 in, it will want more timing in it. The 18 degrees initial is not enough. And it will wake up you 60 foot.

Agreed and if you need a bushing to increase initial/limit mechanical, I have 10 and 14* bushings. $10 + shipping.

Find the point it kicks back on your starter when hot or highest vacuum at constant RPM while advancing distributor. Run it at the lower point of the two.