Most left-wing seat held by a right-wing party and most right-wing seat held by a left-wing party...

[Filuwaúrdjan]

It is certainly a seat that would usually be safe National, and it did have the highest National + ACT vote  in a seat represented by a Labour MP. It is a rural and small town seat in south Canterbury (so south of Christchurch). It is more socially conservative, with a 59% no vote for legalising cannabis. Labour also benefited from the incumbent National MP resigning in disgrace for sending unsolicited pornographic messages to at least five women while they had a strong local candidate.

Some of the rural bits towards Christchurch aside, it is very much traditional Labour territory though.

[Filuwaúrdjan]

Is this to say that Rifkind losing in 1997 was a sign of demographic change in the Pentlands area of Edinburgh?

Different part of the city. The last Conservative MP for Edinburgh South was Michael Ancram who lost in 1987 (and then re-emerged as MP for Devizes in distant Wiltshire).

[Pericles]

It is certainly a seat that would usually be safe National, and it did have the highest National + ACT vote  in a seat represented by a Labour MP. It is a rural and small town seat in south Canterbury (so south of Christchurch). It is more socially conservative, with a 59% no vote for legalising cannabis. Labour also benefited from the incumbent National MP resigning in disgrace for sending unsolicited pornographic messages to at least five women while they had a strong local candidate.

Some of the rural bits towards Christchurch aside, it is very much traditional Labour territory though.

Rangitata is more rural though, and voting patterns aren't the same as they were in the 1980s. The seat is currently safe National outside of when Labour benefits from a perfect storm and wins a nationwide landslide.

[CumbrianLefty]

Edinburgh South has Labour as the tactical unionist choice in a very middle class constituency that has voted Tory in devolved/local elections.

The area really has changed a lot though - there's a habit in Scottish political circles to think of the social geography of the country as it was decades ago (and this then gets copied by the rest of us for obvious reasons) when much is quite different. The inner urban part of Edinburgh South (which was still quite posh until relatively recently) is now full of students and the sort of financially strained early-career public sector professionals who mostly are very much not right-wing economically, even if it's probably not right to think of them as left-wing in classical terms.

Is this to say that Rifkind losing in 1997 was a sign of demographic change in the Pentlands area of Edinburgh?

Pentlands had been marginal in most GEs from 1964 though - even if the Tories never lost until 1997.

[Yeahsayyeah]

Germany (and most of the states) has PR for the seat allocation, but also FPTP districts whose are winners are guaranteed to get seated in parliament.   

From 2004 to 2014 the district Leipzig 1, that was then mostly comprised of the left-wing liberal to left bastions of Südvorstadt and Connewitz was represented by the CDU's Robert Clemen (with about 31 and 29 %) who was as christian conservative as you can get in Germany.

[𝕭𝖆𝖕𝖙𝖎𝖘𝖙𝖆 𝕸𝖎𝖓𝖔𝖑𝖆]

I am going to use mayoral results for the Italian version of this exercise like some fellow Latin posters have done - even if the current Italian electoral law technically has FPTP districts using them would be quite a mess for a host of reasons.

Limiting myself to sizable cities... the most right-wing one to have a mayor on the left is (or rather is about to be) Verona, a traditionally safe conservative stronghold which elected a CSX mayor just two days ago partly thanks to a stupid split on the right, while the most left-wing one to have a mayor on the right would be Siena, an important centre of the Red Regions heartland which hasn't budged in national elections but narrowly went for a CDX mayor in 2018 (I suspect that had a lot to do with the Monte dei Paschi di Siena bank scandal).