If we finish first in the group, it is really important that Napoli does so too (unless they finish third).
If we assume the difficulty of different opponents in four layers (this can always be discussed, for example, are Dortmund really so much worse than Real, etc. - I would certainly rather face Dortmund than Real though):
1) Bayern, Real, Barca
2) PSG, Atletico, Dortmund, Arsenal, City
3) Leicester, Porto/FCK, Monaco, Leverkusen/Tottenham, Benfica
No easy games, but i would say we would be favourites against all teams from tier 3, and have 50/50 encounters against tier 2 while being underdogs against tier 1 (roughly!!!). We assume that facing two teams from the same tier will be equally good/bad for us, though some might argue drawing Arsenal is favourable to drawing PSG, the difference might not be large enough for us to really be able to say one is a lot easier than the other.
Now, it is probable that some of Real, Bayern/Atletico and PSG finishes second. It all comes down the Real - Dortmund, Bayern - Atletico in the last round and Arsenal - PSG in this coming round. Therefore there lies a lot of assumptions in estimating which place will maximize our chances of an easy draw. I will put on some convenient probabilities to simplify my arguments, but could easily use for example bookmakers' odds as most precise estimates of probabilities for different outcomes.
If we for a second assume, that Atletico will hold their lead (leading by 3 points) with probability 2/3, that Dortmund will hold their lead (if they win the next they just need a draw in the last game, but it is at Bernabeu) with probability 1/3 and that Barca will win their group, then one of the tier 1 teams will be expected to finish second, and two expected to finish first.
On to the tier two teams. We already assumes that Atletico will finish second with prob 1/3 and that Dortmund will finish second with prob 2/3 while Man City will with probability 1. Since PSG and Arsenal are in the same group, the distribution of tier 2 teams can be expected to be two finishing first and three finishing second.
Tier three teams... Two will finish first and two will finish second. So it all depends on the group of Napoli and Benfica/Besiktas. If Napoli finishes third, which i find unlikely (but they are an italian team so never say never) we will have three teams in each spot.
If Napoli finishes first we will have following probabilities of drawing teams from different tiers:
Juve finishes first: 1/7 tier 1, 3/7 tier 2, 3/7 tier 3
Juve finishes second: 1/3 tier 1, 1/3 tier 2, 1/3 tier 3
If Napoli finishes second:
Juve finishes first: 1/6 tier 1, 1/2 tier 2, 1/3 tier 3
Juve finishes second: 2/7 tier 1, 2/7 tier 2, 3/7 tier 3
From here on, it all depends on how averse you are to draw tier 1 teams for example. If we only care about not facing Real, Bayern or Barca in the first knockout round, then we will benefit from finishing first no matter the outcome in the Napoli group (assuming my estimates of outcomes in Real/Dortmund, Barca/City and Atletico/Bayern groups are close to precise of course).
But it would be really nice to face a tier 3 team, which is equally likely for us in both spots as long as Napoli finishes in the same spot in their group. Which again would lead us to prefer being first (and Napoli being first!), since we would have same probability of facing a bad team but less probability of facing one of the tier 1 teams.
It clearly is best for us to finish first if Napoli finishes first, while it would be the worst to finish second if Napoli finishes first (horrible outcome). If however Napoli finishes second, it really is up for discussion. I think finishing first is still better, though the difference is really small.
All together i would say that we at this point would benefit from finishing first, though the difference is certainly smaller than in previous seasons. At the same time, there is a lot of uncertainty, since so many groups are still open, which means that it is possible we could end up in a situation where a second place is better than a first on paper. An example of this would be if Napoli finishes second in their group and neither Real nor Bayern reaches the first place in their group. Add to this the horror of Barca fucking it up (very unlikely, but my assumed probability of 0 is not true) and we would have a probability of 1/2 to face either Barca, Bayern or Real in the first knockout stage despite finishing first. Just the fact that this can potentially happen with two rounds to go is insane. The best would clearly be if we, Napoli, Real, Barca and Bayern all won our groups, but this is also very unlikely.
A few notes to add:
I believe that the competition this year is much closer, with the favourites being smaller favourites than in previous seasons, while there is a large group of outsiders that could go all the way if everything works in their favour. Also, from the bad teams, none of them seem to be really horrible, maybe except from Leicesters group, this has to be the worst CL group in many years.
If we hit form we can go far, but the draw will have a lot to say this year, the new group seedings have definetely shaked things up, which i tihnk is nice, because i am really all for convergence amongst top teams instead of divergence, where Real, Barca, Bayern etc. allways have easier groups, and because they are good and wins them also will most likely get easier draws - at the same time winning a group like City did last year does not automatically imply that you will have no hard games until late in the tournament. Of course, these things can still happen, and will to some extend, but it requires more luck than before, and i am all for this as this gives clubs with good management and good projects a larger opportunity to challenge the "big three" that execpt from Chelseas win five seasons ago have won CL the last six years, and been overrepresented in the semi finals.
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