I preferred when it was called Heat

In case you don't know, it's about a bank robber doing "one last job" as a romance develops with a woman - previously a hostage - who doesn't know his profession. And it happens in Boston.

1. The first heist is expertly planned. Then the subsequent robberies were thrown together haphazardly for no apparent reason other than to attract cops and create chase sequences. Really incredibly dumb beyond words.
2. The FBI suspects Affleck & Co from the start, but doesn't bother surveilling their activities, except at one barbecue. Basically, had the FBI agents acted like the real FBI (or the fictional FBI in any other movie ever made), Affleck's crew would have been shut down after 10 minutes - and I could have hit the local bar.
3. Rebecca Hall complains that her Prius had bottles thrown at it "in the projects". Affleck and sidekick go to a specific apartment in the projects and beat the ever-loving Bejesus out of someone without ever making the connection between the two. Firstly, how did he know the guy? And - more importantly - why would he even care or take the pointless, pointless risk in the midst of planning heists amidst FBI stings?
4. The A-Team quality skill-level with machine guns is really laughable and looks really dated, but I just threw that in for giggles.

1. Hall, upon meeting Affleck for under five minutes, is pretty much gagging to confess what we all just saw happen, and it sounds like: "Btw, I was just in a bank robbery which I have to tell you because I like you and here's some more information about the robbery which obviously there's no way you're involved in because that wouldn't make any sense." The good news is that she doesn't say fuck very much.
2. Renner (remember the guy from The Hurt Locker?) reminds Afffleck that he spent 9 years in the slammer more times than my mom reminds me I once left my jacket on a bus. Talk about repetitive, and that's in between his incessant ranting about needing "take cayrh of the fuckin' toonie bank bitch". What a charmer too.
3. Postlethwaite meanwhile delivers a slight variant on the "I killed your brother" speech common in screenplays with something to do about how Affleck's mother died like a whore - you know, the sort of thing you'd say to encourage someone to shoot you in the "reproductive area", which (SPOILER!) Ben does at the end.

1. Super-obsessed cop chasing down the hero, and specifically remarks multiple times on how awesome the hero's crew must be and how they need to be shut down.
2. The crew doesn't plan their own jobs - an established character-actor-slash-third party provides all the info.
3. Cops rely on tiny fragments of information from informants to make giant leaps of faith to bust everyone in the crew. Should be picking lottery numbers instead, since it's pretty weak in both films.
4. Cops photograph everyone in the crew at a casual event, but it's ok since the hero knows about it - and tells the cop later! "We've been made, boys!"
5. Cop and robber sit down and have a tete-a-tete about which one is going down first. Great when De Niro and Pacino do it.... not so great when Hamm and Affleck give it a shot.
6. Hero meets a sweet-yet-damaged girl who makes him realize that his awesome lifestyle is really terrible and needs to get out. Naturally, she doesn't know what he's doing but finds out and then hates him and loves him anyway.
7. The cops stake out the last job but only at exactly the point where the gang is leaving with the money. Imagine that.
8. Crew walks down street with machine guns and big bags full of greenbacks - cop sees one member and kills him.
9. Hero disguises himself as cop/security to bypass cops in pursuit. I presume in real life this wouldn't fly, by the way.
10. Cops use girlfriends to ensnare robbers, but girlfriends use magic signals that haven't been previously foreshadowed to save their beloveds. A little cheaty.
11. Hero must deal with final "set things right" killing before it's all over. Even for Affleck, shooting a man in the rhubarb is really a little low.