Models for grinding HSS Lathe Tools

I can only fit 1/4 shanks in my drill chuck in the tail stock. This is on my watchmakers lathe.
 
A slot drill could work but im wonding how much force that would be on steel in a tiny little lathe.
 
Most endmills dont center cut. Drill first undersize close to depth then go through with a slotdrill or flat bottom drill. Thats my method.
 
I was going to use an endmill but then when i got my chuck out i saw it was 1/4 max.
 
So i am in a predicament need a boring bar to bore a flat bottom 5/16 hole 1.5" deep any tips to make this boring bar out of 3/16 hss? I know it is going to take forever to grind.

All good suggestions but I have to ask - what kind of accuracy do you need for this hole? Is it a precision bore or just a simple hole? The reason I ask is because if it is a precision hole then you need tiny boring bar, maybe 1/8" or slightly larger. A steel bar can go about 1/2" deep before deflection becomes an issue. A carbide bar can get you to 1" deep, maybe a bit more.

So, much depends on what the hole tolerances are.
 
I thought of reaming the hole but to get the flat bottom. There is a thru hole of .230 on the bottom of the part with a +.005-.000
 
Could you use the tool post to hold a drill bit or end mill instead of the drill chuck in the tail stock?
 
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