When your A/C no longer blows cold air you have left it too long. The gas has lubricant and seal conditioners in it and when they run out you run the risk of a seal drying out and cracking leading to a big bill to replace. My mum switched hers off all last winter and come this spring it didn’t work as all the gas had leaked out due to dry seals. The bill to fix it (new condenser and pump) is £700, hence why it hasn’t been fixed.
It’s not just for hot weather btw, makes a big difference keeping the car fog-free in cold damp weather.
My A/C has never been switched off intentionally, it definitely helps with demisting in the winter. I get mine serviced (note that’s not just a regas) at an A/C specialist every 2-3 years. It involves adjusting the compressor clutch, cleaning the condenser and a fixture check, costs only a few quid more than the fast fit places charge for a regas.