Another vote for the 360mm Tele Xenar. The f5.5 makes it easier to focus the for instance the 360mm Nikon Tele ED. At the other hand: i always found that the very shallow dept of field when fully open doesn't make it easy to work with and i almost use always a 210 mm for portraits.
When I shot LF I had both the Fuji C 300mm and 450mm.
Something like Fuji L tessar lenses were popular with portrait photographers for that reason, versus their more "clinical" ones. Still very sharp and not soft-focus at all, but with gentler edge transitions.
Teles per se put a lot of extra leverage on the front standard, and might be harder to stabilize. And realize that if you're considering something like an old Schneider Tele-Xenar, they weren't all that good for color film usage. The more expensive Tele-Arton was.
Sinar shutters are still around in several flavors, and for some people make a lot of sense, especially in a studio; but out in the weather, maybe not so much. Having all you eggs in one basket has its disadvantages.
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