Whew, I waited until I read entire thread (skimmed several pages of foam) before I decided to post something on the topic, but that also means my info is now also months old lol.
CW1, ~55yo. who moved here from a city 3 hours away so he can be closer to his daughter, SIL, grand kids, basically family. Nice guy, but him and his family are like Murphy magnets. He's always missing work for all kinds of reasons. Car breaks down, everyone in the family gets a bug, house floods, house catches on fire, alarm didn't buzz, etc. Obviously that translates to less pay and more and more expenses. I feel bad for the guy but he misses so much work that we have to cover for him and it gets annoying. He does come in sometimes on weekends to try and catch up so that helps.
He's living with daughter, grand kids and SIL, and his commute to work is over 1.5hrs so he decided to rent an apartment much closer. Well that didn't last long because it's too much and couldn't afford it so he moved back in with them and is back to driving 1.5hrs each way.
He wants to sell his house from the other city and needed to make repairs and get rid of things, but can't afford it. Then a few months ago the roof got damaged from a storm, then a small fire broke out in the garage and in both instances he had to borrow money to cover the cost before insurance paid (about 2-3k each time minus deductible).
Recently heard; after being here 2yrs and have almost completely settled in, his daughter and family wants to move back to the city where he moved from! But the kicker is, they can't do it unless he helps pay for a bigger house that they want to build from scratch. He agreed, but he hasn't sold his old house yet so they are scrambling now to sell that sooner so whatever they get (very little I'm guessing after so many cash out refi) can be used for a down payment. Even worse, he says when that happens, he will continue to stay here (3 hrs away) so he will also be renting an apartment while also helping pay for the new house!
CW2 doesn't like inconveniences and a little hassle. He bought a new $35k car online with no haggling because he doesn't want the hassle. He likes to buy supplies or equipment for work, sometimes hundreds of $ a year that is reimbursable, but refuses to fill out a simple 1 min. paperwork to do it. I've tried convincing him but he just gets upset. The last time this happened I asked if he could buy me some things without having to pay him back, he just wandered off.
He also had a couple of friends on his cell plan that he continued to pay for hundreds/mo. even after they have already gotten their own plan. He said he didn't want to spend time changing his plan. He buys tons of toys and gadgets that aren't useful or just get stored. Like a $400 3d printer that he printed a couple things and no longer uses.
He's single and renting a 3 bedroom town home from a friend for over 10 yrs. He can rent something cheaper, but at least the friend has not raised rent in all those years. I suggested why not offer to buy it since it's actually quite affordable and he is obviously not leaving, but he is not interested in talking about it to him (his friend lives out of the country btw and just hung on to the property because he obviously found a cash cow).