Oak flooring & undercutting skirting boards

[Bearcat]

We are thinking about having oak flooring put down through most of our downstairs.
One floor fitter has said that his preference is to rip the 1930's skirtings off and replacing them with new which we will then paint. He would do the undercutting of the skirting boards if we wanted (to slot the oak under, therefore no beading) but obviously wasn't so keen.
The next guy who came to quote was quite happy to undercut explaining all the pro's & cons and although a big job was no problem and he would do a good job.
Has anyone gone for the undercutting option and how was it? We realise we may have to paint the skirting boards because of chipped off paint.
Basically if we are going to go for this we want the best look possible as the flooring will cost a small fortune.
TIA.

I ditched the carpet and did the living room in engineered oak I took the skirting boards off and put new skirting in at the end of the job. Soooooo much easier and nicer looking.

I had to undercut door jambs.

My carpenter says he tried undercutting existing skirting when he did his own house and it was a nightmare, (lots of dust) - he didn't recommend it.

Surprisingly my old skirting came off without any plasterwork damage and the new skirting was only a few quid a metre and being new it makes the room look crisper.

If you do go for new skirting a tip is to knot, prime and gloss it before you fit it. Then you only have some touching up to do. Otherwise you have to mask the new floor and paint very carefully to avoid getting paint onto new oak floor.

You can order the new skirting ready primed. (I did, but they supplied unfinished and I had no time to prime it before fitting - was quite a job masking many metres of new floor).

Just asked my carpenter husband and he has agreed that it is a nightmare job to do.
He made a good point that by the time you factor in the extra labour cost of doing the undercutting it wouldn't be much more just to put new skirting round.
You would obviously also loose a lot of depth on your existing skirting which won't look as nice.
We have solid oak throughout downstairs with new skirting and he undercut it under the door frames, looks fab

It depends what quality upon plaster is in, I
Have lived in houses were the plaster was held on by the skirting!

Anyway if the fella says he can replace it, I think that would be the nicest option, least mess and most professional finish.

Thank you for your replies.
Very helpful.

We had the skirtings taken off and replaced (in fact, in most cases the original ones were re-used). My carpenter also rejected the undercutting option as being much more tricky.

He was right; taking off the skirting caused far less mess than I expected. There was obviously some repainting, but the end result was really smart.

That was in the hallway, but in the playroom we just left the skirting and went with the added beading. There is such a lot of furniture in there that you never actually see the edges of the room, so it doesn't matter! But in the empty hallway the clean lines were much more important.