As with so many things in life, I think 'it depends'.
A holiday where the hotel is essentially the destination is very different to a packed activity holiday where you are in your room to sleep and that's about it.
The rating systems are also not foolproof. While a four star hotel will likely have some amenities that the two star lacks, if you don't use those amenities that can be irrelevant.
A shabby, run down four star with bar, lounge and ironing board in room and overworked, demotivated staff managed centrally as part of a global chain whose management are going through a rocky patch may indeed not be better than a two star spotlessly clean hotel with lovely staff who love being hospitable and for whom nothing is too much trouble.
Generally, I would have fewer days away to allow for some break between finishing work and going away to avoid the doing the washing at 2am and last minute packing nightmare.
DH and I have both travelled a lot for lewisite and business and could any hotel which is clean and where there is not a fire drill in the middle of the night when you have an early start to be a win.
I'm not sure this helps you, best to start with thinking carefully about what you really want and go from there. Even personal recommendations can be tricky, in the face of staff changes
Hope you get what's right for you.