I always manage Liverpool, so I guess I'll chip in here.
Expectations: I opted  for Champions League spot in the season expectations, but in retrospect I  should have gone with Title Challenge as I won the first season fairly  easily. This is probably one of the main reasons I can never get more  than 4-6 years done in these saves, but it's still fun as Liverpool is  the only team I support. Anyway.
First transfer window was mainly  about rebuilding the squad. Get rid of some deadweight and get some  real talent into the ranks. That meant getting rid of players without a  future at the club, loaning out youngsters to free up extra wages, and  replacing squad players with quality players and prospects.
Notable players sold: 
Allen, 
Borini, 
Johnson, 
Mignolet, 
Skrtel, 
Assaidi. Also got rid of 
Jones and 
Touré.
Notable players bought: 
Verratti, 
Tielemans, 
Sven Bender, 
Balanta, 
Lucas Romero, 
De Sciglio, 
Quintero and 
Szczesny.
Transfers I regret doing:  Buying 
Sirigu as I was able to snap up Szczesny right after who is much  better imo. But I was able to sell Sirigu in Janurary for almost twice  what I spent on him, so it wasn't all bad. Also, 
Hachim Mastour, Alper  Ademoglü and Josh Murphy don't seem to be developing as I had hoped, and  although 2 of them were cheap I did spend £9m on Murphy that might  prove to have been a bit much.
View attachment 701923
Note  that the De Sciglio transfer is listed as free, this was due to a beta  bug where the instalments simply disappeared from the transfer fee. And  since the whole transfer was in instalments, I ended up getting him for  free. Didn't notice it until a while after, but to be honest it really  helped financially so I CBA to load an old save 
Several of  these transfers were paid with instalments, so I'm gonna be noticing  that in the monthly financial figures for a couple years.
Second transfer window (summer 2015):
View attachment 701920
One  transfer stands out here: 
Paul Pogba for £80m. £40m upfront + £40m over  48 months. Didn't plan on this, but after he became unhappy because I  enquired about him, saying he wanted to move to Liverpool and asking to  leave, I knew I would be able to afford him. 
Also splashed £21m on  
Jonathan Silva, very promising left back to rotate with Moreno (and can  also cover on right back). Hasn't quite developed as well as I hoped,  but still a good player. 
Munir became available for £14.25m after I  missed out on him in the first window, so I had to get him. Great  player, is already worth over £20m. Also signed 
Papadopoulos as cover  for CD and DM, although I didn't really need him. I'm in January 2016  now and he still hasn't played a single match for me, and I'm surprised  he hasn't complained yet. Will be allowed to leave as soon as he starts moaning.
But, to afford Pogba and Silva, and  also keeping the wage budget to a minimum, I let 
Enrique, 
Lallana,  
Henderson and 
Verratti go for a total of £100m. Had some real trouble  offloading 
Lucas, really just wanted to get rid of his £75k pw wages as  he was not playing at all.
So, after some tweaking with the tactics, I ended up with this:
View attachment 701917
Usually  played with 2 MCs, but decided to pull one of them back to DM for a  couple of reasons, mainly defensive but also simply for having some  great DMs in the squad. Trying to rotate as much as I can, and have  mostly been able to keep the players happy with a few exceptions: Moreno  got his first Spain cap and has been moaning about a new contract ever  since. I'm not budging and he still has 3.5 years left on his current  one. Sterling just requested a new contract, but when I told him he'd  get on at the end of the season he went all primadonna and demanded one  right away. I'm not budging for him either.
Currently down to  £1.6m pw wages, which is lowest of the top 6 clubs. Very pleased with  that, but I know it will increase rapidly as contracts are up for  renewal soon.
As for general thoughts on the Liverpool squad, it  is good enough to challenge for a top spot without major changes like I  did. But I would strongly suggest selling Johnson as he's on around  £100k (if not £120k) pw, 29 years old, and possible to get a decent  price as well. Touré is also expendable with his £70k pw, and you can  replace Borini with Munir in the first season without losing any money  on it. Apart from that, I'd look at the keeper position. Jones is far  from good enough, and Mignolet won't cut it in the long run. Not  necessarily a priority, but if you got the money I suggest you spend if  the right replacement becomes available.
The last thing I'll  mention might be the most important thing: The backroom staff. They're  pretty much all useless. I terminated ALL contracts except ONE, which  was Andy Renshaw (U18 Physio).
View attachment 701931
Not sure how the training overview would've looked with the original staff - I didn't even bother to check, I just browsed through their stats - but it definitely wouldn't have looked as good as this:
View attachment 701928
So all in all, if you're gonna play with Liverpool, I highly recommend considering the following things:
1. Offload deadweight and high earners not justifying their salaries.
2. FIND NEW STAFF!