should I buy the nicest house on the street ?

This is a difficult question that we can't answer for you however, below is some food for thought and a start of a conversation on an important topic.

The answer to this question will depend on a lot of factors, including but not limited to your financial situation, your personality/lifestyle type, and the neighborhood in which like to move into. That is why is so important to seek advice from local agent who knows the vibe of the neighbours because the answer to this dilemma it has to do as much with neighbours as it has to do with the potential house condition. The demographics or general sentiment may not match your personalty so may end up not liking your neighbours therefore eventually may need to move out of the area.
The first thing is to figure out what you are looking for in a house. Are you looking for a place that needs some minimal work or are you looking for something move-in ready? If the home needs lots of work then maybe you should wait since the fixing up the home costs are soaring. If it's move-in ready then maybe it's worth paying more than what other homes on the street are going for in order to get exactly what it is that you're looking for.

We can't tell if  either options is something worth doing without knowing more about your situation and lifestyle preferences. 

There are two schools of thought on this:

1. Buy the nicest house on the street to make your neighbours feel inferior and they need to pay higher taxes.

2. Buy the nicest house on the street so that you can make your neighbours feel good because your improvements hence their house value go up.

School of thought 1: If you buy the nicest house on the street, it will make your neighbours feel worse about themselves and what they have achieved in life, which may lead to them becoming jealous of you or even resentful towards you because they think that you are bragging about what you have done with your money and trying to show off. This is not a good idea because it will create tension between yourself and your neighbours. 

School of thought 2: If you buy the nicest house on the street, it will make your neighbours feel better about improvements on their street. 

The answer lies within yourself and soul searching will help you lead to the right path. 

p.s.  Next time you have a discovery meeting with your agent see if this question comes up.