[jumpka]

If I wanted to spend the money (not sure if I do), would I be better off with Westone UM2 phones, or $70 Etymotic E6i phones (or $110 Westone UM1) plus custom earpieces? With the cost of an audiologist visit for fitting, the prices would even out.

Suggestions?

 

[Indygreg]

No real answer for this, but I would 100% get the UM2. Get a shure fit kit for a few bucks extra and odds are you will find a fit that is plenty good enough for you. Get the best IEM you can for your money and assume it will fit.
Then down the road you might consider a custom tip, but many will be happy without them.