Amp recommendations

@safebelayer
Thank you for the response. My plan is to have my 300B amp accessed and hopefully repaired. I did find someone local to me that came highly recommended. After talking to him, he sounds like he knows his stuff. But if you could send me Pat H's contact info, I'd appreciate it very much.
I looked online for Dennis Had and the only contact information I could find was through his EBay store. I sent him a message through EBay but haven't heard back from him.

This entire discussion has me thinking about upgrading my speakers to something like the Klipcsh Forte III and selling my Chapman's. If you could educate me a bit here. My 25W 300B is under powered for my 90dB Chapman speakers. I listen to mostly jazz and some pop. I rarely listen to anything at high volume as my system has always been more than loud enough at low volume settings on the preamp. At low volume settings, is the load on the amp too much or would that only happen at higher volume settings?
I guess everything hinges on how things turn out with my 300B amp.I should know more next week.

Buy a used Krell Evolution 302, 302e, 402, or a 402e. You won’t regret it. There are a couple out there to choose from. 

"Just Listen"...to you! "Love the sound", "Don’t feel you have to turn it up much", "20+ years on the tubes"," Listen to jazz and some pop". First, it does not surprise me one bit that you need to replace the tubes....way late! But, since you never felt the need to turn it up much, maybe it wasn’t overdriven and therefore need to have (all/though probably some) of the caps and resistors replaced. Most of the time, problems with tube amps are the tubes. Try that first.-Your least expensive option.
Keep your speakers if you like them. Use 4 ohm taps on your amp (maybe, always listen), but tubes generally do like 8 ohms better. Have fun listening to more modern 8 ohm speakers at shows in the meantime or try buying used well-reviewed 8 ohm ,more efficient speakers here on Audiogon. Speaker design has improved in 20 years!
Moving up the power tube chain will likely lose some of the "aire" and Magic that I think you’ve become used to with the 300B’s. However.....
Parting thought: You might try a Croft Series 7RS Hybrid amplifier if you get a chance.

@z32kerber
Because you stated "I’ve always loved the sound", the following list starts with the highest priority:
1) Get your Cary Audio CAD 300B working again.  Finding a sound you love is the holy grail of audiophiles.  As amplifiers age, the sound quality gradually diminishes as the parts wear out.  You may not have noticed as this is a very gradual process.  Refurbishing/upgrading parts (tubes, capacitors, resistors) should at least bring the sonics back to the original level.
2) Get the designer's (Dennis Had?) opinion on what to do along with suggested other amps
3) Contact Cary Audio to get opinion on what to do along with suggested other amps

If you change your amps and/or speakers you will get a different sound, likely an upgrade but no guarantees that you'll like the change.  

With your budget, get a pair of VTA M125 mono block amps at 120 watts each. You can build them as a kit for all of $2300, or get them fully assembled and tested for about $3000 - less without tubes.

If you feel that you don’t need or want that kind of power, VTA has the ST-120, 60 wpc tube amp which is a Mac 275 killer. Full kit is $1200 and fully assembled/tested at about $1700. Without tubes fully assembled is $1455.