A little kindness goes along way.
If he is an actual friend who would do the same for you, absolutely offer him one on loan unless he is some couch surfer or unemployed bum. Invest and risk nothing EVER in these types of people.
Definitely under no circumstances lend something irreplaceable though. No one NEEDS to borrow a master built SRV strat, or pre-war Martin for instance. Look up the story of Johnny Marr of the Smiths loaning not one but 2 rare Les Pauls to to the Gallaghers/Oasis. One was destroyed and the other held ransom, neither ever were returned to Johnny.
That's exactly my difficulty. Right now only have favorites and most quite irreplaceable. He's got cash, I'm trying to get him to get a CV of his own. He very well might and we can welcome him here. Solid dude.I've lent out guitars that I don't often play. My favorites and high end stay with me but the others like to be played too.