In my job as an electronics engineer I have been using a lot of usb to serial adapters over the years;... and learned A LOT.
Here is what I got out of it:
The majority of adapters are designed with either a FTDI chipset or a Prolific chipset. There is also a lesser known called Silicon Labs.
Compatibility with the operating system (Windows, Mac, Linux) on the USB side depends on the drivers and the chipset inside the adapter.
Compatibility with the serial device on the serial side (RS232 or RS485) depends on the chipset and the serial driver chip inside the adapter.
FTDI chipsets are higher priced, works well with most operating systems, and if you have a usb serial adapter with a good serial driver chip it will be compatible with most serial devices as well. FTDI is designed in Great Britain.
Silicon Labs chipsets are also very good, similar to FTDI. Made in Texas USA.
Prolific chipsets are low-cost and often, in my experience, incompatible with many serial devices and also has problems with the never versions of Windows (Vista, 7); but usually works fine with older operating systems (Win 2K, XP). Made in Taiwan. Usually sold on ebay.
In my younger days I have used many Prolific based adapters with a lot of headache, I now only use
FTDI based usb serial adapters from reputable sellers, now without the headache. Im sure I could have less gray hair now if I just had used FTDI adapters from the start
Here is a good
usb serial wiki which will tell you everything you need to know about usb serial adapters before you buy.