Mistakes I’ve made

Lot's of Mistakes in my life.  "Loaning" out motto,
"Never loan out anything I or you are not willing to give away"
Stereo equipment, tools, money, frying pan...

OP: Never regret being generous. It's a an admirable character trait and you will be rewarded many times over.

+1 @kingsleuy
+1 @middlemass
Stuff and money comes and goes, but what should be a higher priority is relationships.
Generosity is a great virtue, but it must be tempered with wisdom.  For instance, if a guy keeps running out of money because he cannot control his spending, he cannot distinguish his needs from his wants, then any additional money won’t really help his problem.  If it is a loan, you’ll only be adding to his burden which he cannot pay back.

I loaned kenjit a pair of speakers and when he gave them back he had drilled holes in the back to tune them to his liking.  Something about the back waves now being able to escape versus bouncing forward and commingling with the forward firing waves.  Way over my head.