I've been wondering that for a long time, too, Jillpie! The last "paid position" that he had was working for / with Liza in ColMar Enterprises (an offshoot of Chandler Enterprises, when Liza was at odds with Adam, for a change). Ever since he (and Aidan) have had his (their) PI business, it seems that he does more work "for himself" than for anyone else (ie: helping Liza and Colby go into hiding, helping Babe and Jamie escape, doing research on Erin and Dixie, etc.) They never show them having any paying clients!
On a similar note, perhaps someone out there remembers this. When Tad was heir to the Orsini fortune, he put all of the money in trust for Jamie - that's why he started his original PI business to begin with. If all of that money is in trust for Jamie.......and Jamie is presumably not only over 18 but over 21, now.......how come Jamie has to continue to live in squalor or "needs" Phoebe's money??!! I know that JR is banning him from college and med school admission, but he could at least use some of the trust money to live in a more comfortable apartment and buy "real food"!
The whole thing with Babe and Josh was disturbing, and Amanda made me sick, today, as always.
It would be very weird if Di(xie) turned out to be Lainie or someone else, now that it seems that whomever-she-is is going to get together with Tad!