I'd agree that if you insist on developing loads that are at the extreme of what the cartridge can handle, you will eventually regret it.
A "good" load, in my opinion, doesn't show pressure signs like flattened primers or heavy extraction forces and the powder fills the case very close to the bullet base or even a slight compression. The less "air space" in the case, the better. I've had my best accuracy with loads that are just short of being compressed (case full to bottom of neck).
You'll probably have to use the powder burn chart and some experimentation to find the best powder/bullet combination for your rifle, and a chrono is a worthwhile investment.
