Why I would like Mourinho:
He can be charming and witty, and his time at Porto, Chelsea (2004) and Inter shows he can really bond with players. In his early days at Chelsea he had them playing really dominant, attacking football. Solid at the back, yes, but also with Robben and Duff and co let off the hook. Its the sort of format I think could really work with our squad. Then of course, there is the winning. This guy knows how to win, and how to instil that into his squad. There are plenty of positives to see with Mourinho, if you look for them.
Why I would hate Mourinho:
His most recent appointments have all seem him deteriorate into a sneering, horrid, nasty piece of work. The football offered up by his teams has been awful, restrictive, strangle the game to death type affairs. He has publicly berated and alienated players. He has NO history of actually developing players, specifically young ones - which is at odds with how we run as a club. And he has that 'Arry like quality of buying old mercenaries and leaving a club with an unsustainable wage bill and expensive restructure needed...
Why I think we might just end up with him:
Seems to me he has a good relationship with Levy. We were interested in him way back in 2004 (2003 maybe) just before his reputation exploded and he went to Chelsea, and Levy is a bit like a Mountie - he always gets his man (eventually). He has also had a nice break, which means he is currently the charming, affable, fun Mourinho. The one who speaks well, seems reasonable, and has enthusiasm. Considering his record, it seems a no brainer...
Why I think it would be a disaster:
Ultimately, I cant get past the fact that his MO runs contra to the clubs. He isnt a manager to buy young players and improve them. He isnt a manager that will accept not getting his targets (either "at all" or "on time") and get on with things. He isnt really a manager that works well under pressure, the cracks show pretty quick with him IMO, and at Spurs he wont have the luxury of parachuting into the best team in the league - he'll be under pressure to improve the club.
I would predict he would come in, make us solid, things look good for a while. Then around/after the first summer window things start going sour, his surly and agitating nature returns, and then its a slow demise for his time here...
Why I think it might just work:
Mourinho is a manager, more than coach. If he can get the right coaches in around him, things could get interesting. Just as, taking Spurs to the league title would really be his greatest achievement - and I wonder if he might be motivated by that sort of challenge. There is always the question with his career over the resources he has had at hand...
Levy may well be just the thing he needs. Again, much like 'Arry, having some restrictions might just bring the best from him.
In all honesty though, as much as I could convince myself of some positives, I really think its just got disaster written all over it. AND, given his being settled in London, his record, and availability, I also think us getting Mourinho is the most likely outcome.