Why would you not even consider re-chambering the H-D to .357 Magnum? This has been done numerous times and many 38-44 revolvers have been done over the years. This would be less obvious, less intrusive, far less costly and have less effect on collector value of the revolver than replacing its cylinder! The cost would only be about $100 for a chamber reamer and cutting oil!
Yes, I realize there are reasons for not re-chambering the gun, and if you want a N-Frame .357 a Model 27 or H.P. would be a better solution than re-chambering the H-D, but then I have several .357 S&W revolvers of several models.
As long as you own the gun there would be no issue with the re-chambering. If you were ever to sell it simply be honest about the fact it has been re-chambered and let potential buyers decide. Since you do not mention re-marking the caliber on the gun I assume this is not a concern to you.
I also have an early 1950s Outdoorsman that I wouldn't change simply because I wanted it because of what it was and I have no reason to want to change it to a .357 as noted.