I'm ok with him. He was playing well under Cheeks and dropped hard after he was fired. He's definitely not the biggest problem we have as he was producing. The Smith/Monroe problem is a bigger deal and things change significantly if one of them is traded and we get another shooter on the floor.
I think Jennings's biggest flaw is not being able to finish at the rim and what's worst is not making the decision to drive and score because he can't finish at the rim. I really do believe if he gets better at that aspect of the game, his offense will balance out. He'll take less mid-range fade-aways. His shot is unorthodox and will never be any better just like how Iverson's shot was. It goes against the fundamentals of shooting. The third flaw of his is in pick and roll situations. He just doesn't know how to play it and I think it's because he doesn't drive. That takes away an option at which point he would either pass it or shoot. Because NBA players know that he won't drive in, they'll be focused on the pass at which point he would either shoot it or pass it to the side and end the pick and roll. I think if he works on his finishing, his offensive game will balance out. In the end, he's a good passer and a decent shooter. The rest of his flaws fall on his decision making which if we have the right coach, he won't be taking as many stupid jumpers. He's definitely a talent and can be fixed. But eventually we'll definitely get rid of him. He's a loser.
He doesn't play defense. He just goes for steals.
All in all, I'm not a fan of Jennings and we can definitely have a better PG. However, he's actually the best PG we've had the past 5 years and he's definitely not the biggest problem we have on the team. His contract is reasonable. But I don't think that matters as he's cancer without the stardom.
Smith, on the other hand,

Here's the problem with Smith, he's dumb. Simple as that. He's dumber than Jennings. He's like a really good role player that has to start. But he's getting paid like a star and given the role of the star on the team. I do believe that Smith is fixable with the right coach. But he needs a PROVEN strong minded coach. Maybe Hollins, but I'm thinking Thibidau type. His contract is almost toxic. I do believe he plays for 80% of it. He definitely helps with numbers on the stats sheet but definitely not on the winnings column.
As for defense, Smith was once considered as a candidate to be the defensive player of the year. So let's say he was once one of the Top 10 defensive players in the league and that's great. This is the part that separates him from Monroe! This is what I look at. Offense is easy in the NBA. You can score with the right plays. It's just X's and O's. But defense is very difficult to get!
So let's talk about Monroe. Only flaw I see in him on offense is his shot and it's big because we have a monster that can't shoot called Andre Drummond. I just don't see it getting any better after 4 years of playing in the League. I think it's a mental thing over a capability which is what separates an NBA shooter and a plain shooter. I'm not asking him to be Bosh or KG shooting that mid range. But I think he needs to shoot like Cousins or Jefferson. That's crazy to say because they're actually really good mid range shooters. Monroe won't get a max contract and I wouldn't match it if he does. You don't give a big man that type of money when he can't shoot the mid range jumper. He's NOT Drummond!
On defense, no effort! This is what separates him from Smith. Monroe will get a Jefferson type of contract before he went to the Bobcats. I believe he'll get around 12 mill a year and he doesn't deserve any more. He's very overrated and I don't believe he'll get a bigger contract. The new GM would be stupid to match anything more. He's not worth it.
With that said, based on the talent and contracts, with a 2 mill difference projection, I would definitely pick Smith over Monroe. Why? He plays defense. Yes we haven't seen him play defense very well here in Detroit but he's definitely proven it and that's enough for me to keep him. Not because I want to but because we're choosing between the two players. Also, although Smith is a very bad shooter, he can actually make a damn shot and has the confidence to take a 10 footer and beyond. That goes against Smith but it doesn't clog up the paint for Drummond because, after all, who are we building around? Drummond of course! Another reason of why I pick Smith over Monroe is because we can get SO much for an overrated talent like Monroe. We can easily trade him for Barnes and I'd be happy with that. Maybe we can even get Gallinari, that's huge. You never know what'll happen. We don't know what we're getting at the Draft. We might get super lucky and get the Top 3 and get Parker or Wiggins. I like to dream. Or we can get a PG like Smart or Exum. We can trade Monroe for a SF or a PG along with Jennings depending on how the draft goes.
I think this team is very fixable in one offseason and it all starts out with the Draft. Let's hope we stay within the Top 8 and get our pick back because I do believe if we lose the pick that it won't break us but it'll push us back a year. If we get lucky and go into the Top 3, we could be moving forward with two players having potential of stardom and who wouldn't want to coach that. Bottom line, our pick this year is very important to have and could actually make us something great.