but my perspective is more from a hassle perspective.

With multiple guys, most of whom cannot remember where they got the tool from, much less where it is supposed to be returned to............it is a hassle for the employer to keep things smooth when there are potential nasty feelings about "my" wrenches vs "yours".  My Main Man insisted on bringing to the shop his "new from Christmas" Sears rolling tool box several years ago----------but only after we had a somewhat heavy discussion about the possibility of it getting banged up and me telling him that I would then buy it, etc etc........which, frankly, is still too loose for my tastes.........but time I think has made that work out ok-----but I would not do it again.

A good wrenchman has to have decent tools..........that said, they don't have to come from the XYZ High Priced Company..........I see more tools lost in the fields than are broken due to poor quality.  So, I set the tone for the tools bot for the shop.

If I were in the er's shoes..........providing a pu is a good deal for you the ee, but it has to be a better deal for the er.......I know it is for me.  Depending upon the guys to drive their own vehicles, taking a chance of dents and scrapes and busted trannies due to whatever........not worth it.........buy the pu and get it under the liability ins umbrella. 

Paying for the tools---------I would like some kind of list to look at, just to make sure the "surprise" element is minimized.........and, many times at our shop, since the guys do a pretty good job of controlling expenses, that also sometimes translates into NOT dong things or buying things as extensively as they should.........which if I see the "blueprints" ahead of time, I can shortcircuit that.

Sounds like your er is a reasonable guy.........keep him in the information loop........few successful business people, in my experience, like surprises, even though they might not do a good job of laying out the boundary lines ahead of time.