Most forgiving high end speaker 10k-20k?

Look into speakers by Sonus Faber (Cremona M), Vandersteen 5 or 5A or Quatro Wood, Silverline (as Newbee offered),many of the British made speakers are "kinder and gentler". Also, you can get some of what youre after by careful component choice-my TW AKustic Raven One turntable tends to soften the music very slightly to the forgiving side and thats what I like. Stay away from cables and interconnects like Nordost which tend to make things a little hard or steely (less forgiving). A forgiving cartridge like the Clearaudio Virtuoso Wood can get you there too. I realize some prefer to have their system speak only the unvarnished truth and thats just fine.

Tannoy.

I second the silver line Bolero speaker. Simply perfect for you based on your comments. I owned them for some 2 years and loved them.

I would also suggest Nola Viper Reference speakers.

I recommend these a lot, but it's because they fit the bill yet again. The Legacy Focus 20/20's. They make bad recordings sound awesome(they are a warm relaxed speaker, yet deliver dynamics to be exciting)and make great recordings sound amazing. I've had them in 3 rooms. 1 large, 1 medium, 1 pretty small. They sounded great in each one. If you can listen to some Focus, I would bet you would enjoy them. The new models are around 7k

Also the 20/20's were amazing with any types of music (jazz, rock, classical, rap, etc)

Dali speakers are "forgiving" or "easy to listen to." TAS calls them speakers you can marry for life, and Michael Fremer gave them a good review in Stereophile. You can find the review on their website.

There are a couple pair of their "Euphonia" line MS5 for sale for $7,500 and $8,200 right now. This is their top of the line normal floorstander type. They could be what you're looking for.

I own their Helicon 400s, which is one step down from the Euphonia line and they do sound good.