I'm running a pair of Thiel CS6 speakers with a Krell KSA 300S amp. They were about $9000 in the mid 90's. I've been to 3 audio shows and I've found that my system holds up to pretty much anything costing under 6 figures. I've heard speakers that do one thing or another better than my Thiels but I haven't heard anything that would blow them away until the price gets into the stratosphere. A good example of a speaker that is clearly above what I own is the MBL 101E MkII. They are around $90K but if you get a chance you should hear them to see what is possible.
If you can swing it I would recommend going to an audio show to get a broad overview of what is available. The Capital Audio Fest is coming up in November and it would be an excellent way to hear what's available and narrow down the choices.
The speakers that have impressed me the most are from Rockport, Rosso Fiorentino, Dynaudio, Joseph Audio, Sonus Faber, and Paradigm but that's just my taste. These were all speakers under $50k.
About the fear...... If you spend tens of thousands of dollars on new speakers I'm pretty sure you will like them just fine. At least you're not twitterpating about cables.