Tonbridge or Winchester? Rightmove links. Rightmove psychosis driving me mad

[TonbridgeorWinchester]

Unreasonable for Tonbidge
Reasonable for Winchester

Winchester pros:
https://www.rightmove.co.uk/properties/94504308#/?channel=RESBUY

>unrivalled beauty and prestige
>I will be at home among fellow snobs
>extended family in area
>3/4 beds depending on setup so could take in entire immediate family in emergency plus future baby's room
(my entire immediate family have precarious living situations. Parents both destitute)
>spacious, double size of Tonbridge
>can be renovated and increase in value

Tonbridge pros:
https://www.rightmove.co.uk/properties/92164008#/?channel=RESBUY

>1hr to LGW
>40 min to Ldn
>no/negligible mortgage needed, mainly cash purchase (great because i fkn hate working)
>exposed beams (biggest compromised i'd be making on winchester..)
>mum prefers this house to Winchester flat

I'm 28 years old, work remotely in finance but want to return to teaching in the near future. Hope to have one baby in about 9 years time.

Which one is a better fit? Will be moving in with bf who will have no stake in the property.

I went to school in Tonbridge, and live nearby still. Nice lively town, great transport links and amenities, and if you plan to go back into teaching, then you have 3 grammar schools in Tonbridge (Judd, Weald of Kent and Tonbridge Grammar), plus (of the top of my head) two other secondary schools, plus Tonbridge School (boys public school)....all within walking distance, so not a problem if you don't drive. There's plenty to do in Tonbridge (I have friends who live there and absolutely love it).

If you can buy that Tonbridge property outright, then go for it. I think that would be an amazing thing to be able to do.

Only thing to check would be situation with flooding - there were problems in the past with parts of Tonbridge flooding, but I think that is now sorted.