RS,
That's a very good description of the work and various markings. And an interesting gun. Someone did a lot of careful machining on it. Let's take this one step at a time:
1. That serial # indicates it's a pre war early 1930s K22 Outdoorsman. No rib on the barrel, correct?
2. <B> on barrel and frame w/o a date stamp on the grip, can indicate work done in the S&W Service Dept. before the gun was ever shipped new but a <S> stamp is more common. The star following the serial number indicates it went back to the factory for something. These could have been two separate events. The usual date stamp for a factory re-work is not one of those you listed.
3. The 95 high on the left side of grip frame is not common but I have seen a similar 86 stamped there which some think could be a date stamp.
The various # and letter digits on the grip do not appear to be anything but the usual inspector stamps at the factory. The 'B' may be for blue but it's usually on the left side.
4. Usage of the star and the rework date stamp varies depending on the time period. After about the mid 1960s the star was no longer used. Date stamping was sporadic from about the same time. So as you can see, this is not an exact science. I am not an expert so hopefully someone with more knowledge may be able to add more info.
5. The work done sounds very professional and expertly performed. But I've not heard of those types of modifications being done at the factory. The factory would not shorten a barrel that way. But we never say never about S&Ws.
6. Getting a letter for $50 will most commonly only state the gun's original configuration, when it was shipped from the factory and to whom; usually a distributor and may not be too helpful. However in the 1930s sometimes they went to individuals so the letter could hold a surprise.
Any work done by the factory after original shipping will not be shown. That has to be researched by the SWHF (see below) after first obtaining the letter.
Firearm History Letter Request - Smith & Wesson (at S&W website)
Firearm History Request - Smith & Wesson
The Smith & Wesson Historical Foundation (SWHF) has digitized and indexed records for the years, 1932-1941
Smith & Wesson Historical Foundation
Hope that's of some help.