I always buy cheaper watches and find they usually last me a good few years. My current one is from Next (got it reduced a lot in the New Year sales) and it doesn't have holes as such but like a weaved strap so the pin fits in through and can be changed and lasts longer than using a particular hole which gets battered. Mind you, I always take my watch, ring and bracelet off through the day at work due to arthritis swelling so although I don't use it all day it is taken on and off more often.
I find that the larger faces are more uncomfortable these days so try to go for a smaller one.
There seems to be a mini watch trend going on at the moment, they have them in Primark on chains and rings!
If you got one which has decent bits for a new strap to fit through either side you could always go for a nice leather plaited wrist band or similar (depending on what you like to wear I guess) to put through it.
I've seen a lot of ones (mainly very cheap ones) with this stretchy kind of stuff which just pulls for you to get it on too so no fastener.