IME Essex flanges tend to leak. They are easy to put in once you've got your head round the idea of making a big hole in the side of the cylinder.
An obvious shortcoming was the max temp of the thick washer they provide, which iirc is 55°, which isn't enough.
A Warix flange is often easier to retrofit than a Surrey, because the existing HW OUT from the cylinder still goes upwards. Depends what you have.
If your pump is getting air in it, I would ask myself , HOW? Be careful, you can't put a check valve in a vent pipe, , etc.
The negative head thing is only about starting the pump. If water wouldn't come out of the tap if opened with the pump installed but not running, you need a neg head pump.
You, or your plumber, need to be aware of cavtation, too. And check for auto air vents...
A lot of "plumbers" aren't very good in this area.
Be aware that if the pump is not installed in accordance with the manufacturer's instructions, especially with regard to heads and pipe sizes, it can fail and the guarantee will be void. Having said that, some instructions are daft.
£300 for half a day's work is quite alot, I'd have thought. I paid mine £300 a day recently.