Are you wanting to jump to 144Hz if you go with a 1440p monitor? and why not a 34" 3440x1440? And i want to add that scaling in Windows isn't nearly as bad as it was on Windows 7. I have a 3200x1800 13" Yoga Pro 2 and have used x2 scaling and it to works great.. except if you have legacy software that hasn't been updated in the last few years. Also i noticed that if you change scaling it doesn't work all the time and might have to go as far as uninstalling and reinstalling apps or even go as far as a fresh install lol.
I also have a 40" 4K monitor with native scaling, which puts PPI at around 110 which is about the same as a 1440p 27". Its like having 4 20" monitors, but much better IMO.