Hello Jerry,
Decisions are not easy and not always (or most of the times) rational. Thought to share my point of view, maybe it will help you in your considerations..
I have 2 drill sharpening machines and a universal Tool and cutter grinder. Spend more or less 2.000,- euros on these 3 machines together. I could have bought a lot of tooling for that money. But in my opinion you should not see the money spend as gone, at least if you buy a quality machine like the Clarkson. If you by a known brand, used machine, in a fair condition you will get your money back whenever you sell it again!! I have bought and sold again several machines over the last years and the only time that I lost most of what I paid was with an Asian produced machine. With all the other ones (European, UK or USA brands) sometimes I lost a little and many times I even got more then I paid for it! Considering this I cannot buy any tooling because I am sure that whenever I decide to sell my grinding machines again I will get my 2.000,- euros back!!
A second Pro to get yourself a nice grinder is that you can buy used, but high quality drills, mills etc (Dormer, Fraisa etc). I normally buy them at model shows for a few Euros and sharpen them at home. In this way I have quality cutters for less then a rubbish Asian one! Since I have a decent drill grinder (Swiss made Optimum) I have thrown away all my Asian produced drills. The geometry of the drill simply is not good, the middle of the drill is out of centre, impossible to grind a symmetrical 4-facet point.
Another advantage of owning a nice grinder is that normally tooling dulls / breaks when you are in the middle of a job. Since I am working 5 days a week it means my work is over for at least that evening and most of the times for week when I cannot resharp my tools. Further I noticed that whenever I get the feeling a cutting tool is getting slightly dull I regrind it immediately. Before I had the grinders I would keep pushing it resulting in a broken drill bit for example because I was putting too much force and with that ruined my workpiece....
If you have the budget available, get yourself a nice used, but known brand (I recently sold my Clarkson MK1 grinder for 3 times the price I have paid for it) grinder. You will have the benefits of owning one and you will get (most of) your money back when you sell it again.
Good luck with your considerations!
Regards Jeroen