If a character is assisting another character in his/her downtime activities, does this assist counts against the allowed two?
Nope, assisting is free. If there are any complications or interesting stuff happening in that action, they’ll be in it together too.
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Downtime actions are more like specific and delineated Fortune rolls, and not Action rolls, because you don’t set Position or Effect. Although, confusingly under Reduce Heat it says to make an action roll, but then lists the outcomes as if it was a Fortune roll, not as levels of Effect. I’m confident this was an editorial oversight but I could be wrong.
Teamwork specifically applies to Action rolls, not Fortune rolls, so I would personally rule that things like Assisting and Lead A Group Action don’t apply. It become very confusing if you treat Downtime Actions as Action Rolls. Setting Position and Effect during Downtime doesn’t seem like it was what John intented.
I would always count the roll as a single Downtime Action.
All that being said, under Downtime, it does state that if you are helped by a Friend or Contact, you get +1d to your roll. So, the question becomes are the other PCs in the crew really your friends?
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A possible interpretation, and I think it is quite valid for the activities on the list, but not in general for everything that can occur during the downtime. The way I read it is different - Page 153 states the following:
Activities on the downtime list are limited; normal actions are not. During downtime, you can still go places, do things, make action rolls, gather information, talk with other characters, etc. In other words, only activities that are on the list are limited.
Following this paragraph and the others below it, where they stat certain activities involve actions and consequences such as stress, normal actions and etc. So if the actions on the list are like fortune rolls and do not generate bad results, what prevents each time the players to abuse the system and have free +1d roll on each of those activities?
Downtime activities are essentially fortune rolls, as Ariel said. There’s no position or effect, they simply do what the activity says.
I allow PCs to assist on downtime activity rolls, but that’s a bit of a house rule – Ariel’s read on the text is accurate.
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Thanks for clarification. I know what to do now and how to address the possible exploit that some players will definitely see and try to exploit 
I don’t see it as an exploit, personally. It costs stress to assist, so it balances out on its own.
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It’s important to distinguish between Action Rolls made during non-Score play (Free Play & Downtime) and Downtime Activities. The later plugs into the Downtime Action economy, the former doesn’t. Fortune rolls (and Downtime Activities) have outcomes, whereas Free Play Action Rolls have outcomes and Consequences, and plug more directly into the Stress economy, as well as the need for P&E.
As far as “abusing” the extra die goes: only permit it if they are actually helping and actually their friend, and make sure they play out a scene so that they can showcase and explore those characters relationships. Having a scene during downtime where the characters explore their relationships is a good thing IMHO, and an extra die on a Downtime Action isn’t going to break anything. Remember that you can’t Push or Devil’s these rolls, but can spend extra Coin.
I would discourage the sort of play were people just say “I’m helping” without being specific as to how and what and why, then eliding the fiction, and rolling the dice. Some Downtime Activities don’t need to be fully played out and can be resolved quickly, but ones that involve multiple characters are exellent opportunities for characterization and drama outside the pressures and tactics of a Score.
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Many thanks for the thorough replies, I have much better understanding on the idea behind the downtime phase and how to handle it properly.
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My rules of thumb for every mechanical action are (1) does it make sense in terms of the fiction? (2) Is there a cost or a risk?
It makes sense in the fiction that scoundrels should be able to Assist (or Setup) each other on downtime actions. But the Assist should still cost Stress, and a Setup should, like any other Action roll, risk complications.
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