I was wondering how other people feel about loaning out their trailer and if they do it. A friend wants to borrow my practically brand new Zieman 5x8 that cost ~$1000. I've loaned the same trailer to him a couple years ago (I sold it and recently bought another one) on several occasions. I never felt 100% comfortable doing it but I have a hard time saying no. I feel uneasy about it because his financial situation is poor. He has CC debt and a couple weeks ago he called me in an overwhelmed manner because he had a $2200 car repair bill that went straight to the CC. He even told me the new sprockets and chains he bought went on his CC. The probability of something happening is low but I still feel uncomfortable about it. I'm leaning towards saying no. Should I say why? Or just say I no longer feel comfortable doing it?