DBIL hasn't had a proper job ever. He thinks he's going to get discovered. He's 36. He's not (though he does get occasional work in his field of choice). This has meant that he has very regularly relied mainly on other low paying work to make ends meet - along with a general attitude that others will help him out if he gets into trouble.
We have quite a lot of money behind us due to a mixture of luck (inheritance on my side) and a very successful business. He quite often says in front of us that he can no longer do this or that as he's no longer got x or y to spare.
This evening, our DS asked (through DH) if DBIL could come and see him (they get on well which is nice). DBIL's response to DH was that his car was in the shop, will probably need to be replaced and that he would come and see us if we bought him a car. Not sure if he was joking or not. What do you think?