A few things ..
SO239 is designed for working up to 300 Mhz Only
Even if one is looking for low loss on 144 mhz then SO239 should not be used..
Also N connectors follow the military standard MIL-C-39012 and is designed for use up to 20Ghz..
But N connectors also are designed to keep their quality with many connect and re connections.Type N uses an internal gasket to seal out the environment(giving it better weatherbility).
Also N works better for Very High power levels.
Will N connectors work better on 27 Mhz..
Yes..However they can cost quite a bit more and are harder to assemble .
For 11 meters/27Mhz i would Not worry about using N connectors unless you plan on using extreme power (and then only maybe)
If however you do go to use N connectors..
Then so too you likely would be using far better coax
(like Heliax or at Very Least LMR600 or better)
I happen to use Heliax LDF5-50A with N connectors ( for HF )
But my N connectors are $175 a piece ( a bit excessive indeed)