Hmmm...
The short answer is, "as small as possible."
Expanding on that...
In my view, the major concern is what happens during the closing and synchronizing transients; since the two circuits are already connected elsewhere, placing them in parallel will cause changes in power flow directly proportional to the standing phase angle across them prior to breaker closure, and inversely proportional to the impedance around the path being closed.
Also pertinent is whether the impedance path around the loop is one of straight galvanic connection, or whether there are intervening step-up and step-down trafos along the way...
Also pertinent is where along the loop the sources of generation tie in, if any, the impedance of their trafos, and the amount of real and reactive power emanating from / being absorbed by the respective site or sites....ditto loads.
I would not have the impertinence to site a "maximum acceptable closing angle" for paralleling circuits, ever; perhaps others with greater knowledge, qualification and experience than me can speak to the matter.
And Bill: in the instance you cite it would make a fundamental difference in synchronizing success whether the incoming generator is at a higher or lower frequency than the system, viz., a "fast" or "slow" scope; I'm ASSuming the units were always synchronized FAST...
CR
"As iron sharpens iron, so one person sharpens another." [Proverbs 27:17, NIV]