One online source gives the year as 1940.
Contact the manufacturer.
The 3/8 drill is one eighth larger.
http://www.searspartsdirect.com/partsdirect/part-model/Craftsman-Parts/Grass-trimmer-weed-wacker-Parts/Model-536773510/0247/1503820?searchedModel=536.7735.100&blt=
by using a drill
http://www.managemyhome.com/mmh/lis_pdf/OWNM/98110089.pdf
They drill water wells, usually with a truck mounted 6 inch drill.
Drill bits not only come in fractional number sizes they also come in letter sizes. The F size drill bit is .257 thousandths of an inch in diameter. A 1/4 inch drill bit is .250 thousandths of an inch in diameter, so size F is .007 thousandths of an inch bigger than a 1/4 inch drill bit.
For coarse threads (13 threads per inch) use a 27/64 drill
A 4 inch drill pipe torque is used for fishing in small casing.
http://vintagemachinery.org/pubs/detail.aspx?id=2832 Guaranteed this is the manual for your saw... It's a 22 inch length table, hard to find saw.
No wont fit, but I have a 42" craftsman grass catcher and would be glad to switch even trade for your 48" catcher
5.105 is 0.201 inch , or #7 on drill gauge. Both are common drill bits.