Benefit Management: When is a Benefit Not a Benefit?

I'm currently well insured, full dental and above average health. All checkups are done or will be done by the time my contract ends. I also get a professional development allowance that I've almost maxed out.

As I get ready to finish my contract, I need to decide how to best spend the untouched eye care allowance of $200. I'm on my last pair of lenses and my glasses are in an unwearable state following a series of unfortunate events. I've already decided to order four boxes of lenses (a year to two year supply) online. This leaves me with about $40.

I'm aware you can order glasses online but I have a really amazing optician who picks out my frames for me and fits them, choosing glasses I tend to be complimented on frequently. He's not expensive and his stock is always well selected. I don't remember what my last glasses cost but my guess is I'll have to front at least $100 alongside the $40 coverage to replace them, probably more like $150.

So is this saving money by spending money, or spending money to save money (the latter, of course, being a bad strategy)?

My professional development allowance is down to about $30, a fairly unexciting amount. Part of me thinks: free money! But another part wonders if the claims process is worth the savings, especially since what I can get for the cost is so limited.

When does the process necessary to claim a benefit outweigh the actual benefit? Equivalent to driving to another supermarket to save $1 on some product?