DH works with someone whose had 3.
First was a disaster - cheap job that looked like a Barbie (plugs of hair). Second (v expensive to fix the first).
Third as hair has continued male pattern baldness so started to have a gap between natural hair and the 2nd transplant.
Apparently wishes he’d never started as it’s cost a bloody fortune and he thinks unless he keeps going he’s going to end up eventually with male pattern baldness in reverse.
I’ve not seen it, but DH says first was awful. Second looked good for 3/4 years. Third was fairly recently so looks ok ish but a bit odd around the pattern of hair growth.
Upshot is DH (who briefly flirted with the idea as started losing his hair late twenties/early thirties) is really glad he just decided to bite the bullet and rock a shaved head - and very fine he looks to me, even if I’m biased :-).
As to the holiday I think there are circumstances it’s warranted to spend on one partner that are similar such an eye laser (so good vision).
Hair transplant less so, though I get the distress this causes many men.
Has he really looked into this properly (have you?)? In terms of potential multiple procedures?
Has he looked at alternatives such as hair systems that are often more realistic than transplants and can be worn for weeks and all activities?
From what I understand it’s not a one off fix, can go badly wrong and in the end he may end up with a worse result in years to come.