To fully re-roof or to partially re-roof?

[Makemeachannelofyourpeas]

@Pigletjohn or other building experts, I need your help!

One side of our (trickily steep) roof is in serious need of TLC and we have a chimney on the other side that we need to take down (leaking horribly and we don't use it).

We've had two builders come and quote: one has said that we only need to do the bad side of the roof and that the other side "has a few more years left in it". The other builder has said that, while the other side is much better there are the beginning signs of wear and tear and that, with the costs of scaffolding being a large part of the cost, we would be better off biting the bullet and doing the whole roof as a one-er. Both jobs would take about two weeks.

Obviously the first quote is much cheaper. They would be using concrete tiles which "wouldn't look any different" from the other side's original clay tiles "after a year or so". The second quote is eye-watering, but all the tiles would match and we don't want to have to pay more in the long run if we're going to have to re-roof the other side in a few more years...

So, the question is what should we do? Any advice or experience will be very gratefully received!

Apologies for not replying sooner.
You’ve had some really helpful advice from others.
We didn’t have a separate quote for the scaffolding and we ended up having the house, a 2 storey barn and three 1 storey barns re roofed and it ended up costing us about 10 times your first quote!!

Prestons!!

Yes, an extremely enormous amount. It was very difficult for the roofers to give us a proper quote. The house is very old and so are the barns, and nobody knew what would be found when the slates came off. All the buildings are all listed too and the National Park where we live are sticklers for rules and regulations.
We also had great fun (not) with the bat conservation people.
We know the house needed work but possibly not that much!!
However, it’s all done and water tight and as previous posters have said, it’s a great feeling knowing that all the roof is safe and sound.