Hi,
My take on your main query is that I would stick with the Chester for a while until you feel competent in the basic aspects of turning. I.e. plain turning, facing, boring, threading (both internal and external) drilling and taper turning. Get to know your machine thoroughly and make a range of stuff, I din't know if you're into model engineering, but that's what most of us are into here – the clue's in the name of the site. What is your eventual intention regarding the use of the lathe?
When you are more confident, and have made your mistakes and errors, that is the time to look into lathes such as Myfords, but why Myford? A lot of folks swear by them, others swear at them. There are many good or better second hand British lathes on the market than Myfords. Take your time, really get to know the lathe well. Look around at other makes such as Boxford or Colchester (a lot of folk swear by these larger capacity lathes), and then start making your decision. Personally, having had experience with Myfords, Boxfords, Colchesters, Raglans etc I now have a Chinese lathe and find it solid, well built and very accurate. Importantly it came with a good range of tooling and equipment.
Regards
Terry