I've pretty much ran them all(except the 465), and the 365/2166 is a great 70cc saw just as they come out of the box. It will have a lot more power than the 61 and he will be happy with the weight, although they have gotten a little fat in some places, ok most places.
Once they break in he will really like them. Based on what you've told us, I would recommend he doesn't waste his money on the 372 as the 365 will do him just fine after running the 61 for years. He can always pull the jug and remove the transfers and grind the one little strip off it if he even desires to do so(he may not because it works great as is). Then there is a muffler mod and a base gasket delete still left on the table without even starting to grind on the cylinder itself.
Hope we can all see some pictures soon of the new saw
![Smile :) :)](data:image/gif;base64,R0lGODlhAQABAIAAAAAAAP///yH5BAEAAAAALAAAAAABAAEAAAIBRAA7)
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By the way the one
@stevetheboatguy has for sale would make a great upgrade for him if he doesn't mind buying used, he shouldn't as he's been using old faithful quite a while it sounds like.
If he decides to buy new please ask him to support his local dealers first and then use one of the AS sponsors if he doesn't have good local support before buying of the net in general.
Best of luck,
Brett