Since I am new to these waters (forum) I would like to cut to the chase. What is the probability that someone would make a weapon mod with only some pencil sketchs (not amazing but not stick figures either) of the requested weapons?

If they are detailed enough and CLEARLY LABELED (i had geography today) a good weapon moddeler should be able to make you weapon. scan the pics and upload them for people to see

It really depends alot on what the weapons look like, how well they're sketched, what you wanted to do with them (is it practical or complicated, is it someone someone would be interested in?) and what rights to the product you wanted to maintain, if any.

If they're good sketches, look interesting, don't have any elements to them which would not work well in Oblivion, or outside a special setting, and you aren't too concerned with how they're used, your chances are higher than not. Weapons generally don't take long to do, it's usually all the other stuff which is what takes time. Your goal is to try and sell a person on why time should be spent making them. Most weapon mods actually end up getting little use or attention because there are hundreds of them out there to choose from, and all you really need is 1-3 good ones.

in that case i will upgrade my sketches from black and white pencil shaings on a scrap piece of binder paper before i follow through with the request. Also how many weapons are recommended to make the mod worth while? Complete set? one? some where in the middle?

That depends
It could have a bacjround story in which case the owner may've had a matching dagger or it could just be a sword found deep in a jungle

how many points of view are helpful when modding, say, a dagger?

Wat?

Expand your question

when drawing a design concept for a sword or dagger which points of view are most helpful for the 3D modeler? side front top etc...

front, and angular side and any definite striking features