In the first variation, 14 rolls leave a shot, but then he hits maybe 4.5 of those. So 11 times your are hit now and you still win about 1/2 of those as he can never close you out. Of the remaining 25 times 14/36 you leave a second shot then 11/36 he hits that second shot. So 3,850/46,656 or 8% of the time you get hit more than the safe variant and you still win maybe 1/2 of those. So your loss equity might go up 4%.

He has after you hit him, 30 pips to make up to get one off. That is an average of 4 to 5 rolls to get one off. You have 12 left. With a man on the bar, you can't pluck 2 at will. Let's say until he comes in, you pluck one per turn. If he fans 3 times, not likely, but it will happen maybe 33% of the time against a 3 point board, you would then have 7 off before he comes on, and maybe a 50/50 gammon chance at that point.

In addition to what you already mentioned, there are 8 more rolls that get him out of your hair from the bar: 6/1, 6/3, 6/4, and 6/5, where if you leave him there he can stay and create possibly another shot 2 or 3 rolls later.

Math above is wrong. Fanning 3 times on a 3 point board is not 33%. 729/46,656 = 1.6%. Making you a favorite to win a gammon. But then you are on roll with 8 checkers left and he is an average of 4 rolls to get off if he comes in immediately.