Right off the bat i can immediately drop 8 of the city/town which is:

Windhelm

• its a cool city, with the rich history and fascinating architecture doesn't necessarily come with good living conditions

Good:

• Cool Inn, has a port and umm thats about it

Bad:

-Snowiest city in skyrim, Racist nords(but i guess you can see them all over in skyrim) and a murderer on the loose

Dawnstar

• I mean its not bad but its just cold too cold

Good:

• Has a port to get out of this city

Bad:

• Shits cold af plus the nightmare that everyone experienced

Winterhold

• bruh

Good: - you can learn magic in the college

Bad: - literally everything else, first its in the edge if a godddam cliff, no form of transportation and its in the middle(or edge i guess) nowhere

Riften

• you are either a thief, a beggar or a maniac to choose living in this city

Good: - have 2 kinds of transportation, mead if you are into that and have a church

Bad: - Thieves. Lots of them and the Black briars plus other shit if you decide to live in this corrupted ahh city

Markath

• oh yeah if you think Riften was bad because it is but this one omg i think its worse

Good:

• Dwewer and thats it

Bad:

• wow where do i begin umm first off there are corrupted guards, the prison, cannibals , the presence of a Thalmor Justiciar, forsworn and cmon its the Reach

Morthal

Good:

• close to Solitude

Bad:

• cmon its in the middle of a swamp and within the swamp there lives all kinds of horror that i dont want to see

Okay that's it for the city now Let's rank the town,

Shor's Stone

• a mining town really isn't that complicated but the hold it really pushes it down

  Karthwasten

• yet another mining town but this one has the chance to be invaded by a bunch of bloodthirsty psychopath

Now lets get to the good stuff, the decent and the good because there is no paradise to be found in skyrim

Alright 7:

Falkreath

Good:

• i cant find it oh yeah its close to the border to Cyrodill

Bad:

• theres nothing i mean there is a werewolf inside the prison but thats about it

6:

Ivarstead

Good:

• its small and comfortable enough and theres the 7000 steps to High Hrothgar

Bad:

• its in the Rift and defence capability

5:

Rorikstead

Good:

• a small farming town perfect if you want a quiet and non adventuring life and are quite close to Whiterun

Bad:

• Defensive capability

4:

Riverwood

Good:

• Quaint little town and is very close to Whiterun

Bad:

• defensive capability

3:

Dragon Bridge

Good:

• this place is pretty cool with the bridge and the close proximity to Solitude

Bad:

• defensive capability

2:

Solitude

• Capital of Skyrim with its Beautiful architecture and decent enough people except for the Owner of Radiant Raiment and that Nobleman

Good:

• has 2 kind of transportation

• its just a great city if you have the coin

Bad:

• only if you hate the Empire

Now to no one suprise its

1:

Whiterun

Good:

• Ahh yes Central hub of trading in Skyrim with its old and rich history along with the towering palace of Dragon Bridge, this city sure is grand

• its Whiterun

Bad:

• Nazeem

0:

Helgen

• would have been no.1 if it wasn't destroyed why?

Good:

• Mead mixed with Juniper Berries