Straightforward if you have the right tools. I suspect an epic pain in the posterior if you don't.
If you're going to drop the pan and do the filter then that isn't going to be pleasant on stands since access will be very limited to get to all the bolts out and then clean everything up and put the sump back on properly. If you over-torque the bolts you can bend the oil pan flange which then damages the gasket which then causes leaks so be careful with them - 10Nm. Personally I wouldn't try this job on stands but I'm sure someone on here will have done it who can report on how it went.
To fill it up again you really need a pump which can push the fluid up through the hole. I believe people have contrived solutions using bottles and long hoses, but really the pump is the way to do it. That's £75-100 depending on which one you get. I may consider lending mine if you don't have access to one. You also need VCDS to monitor the gearbox temperature.
Meyle and Febi do gaskets and possibly filters. Don't forget the o-ring for the filter. Audi fluid is about £15 a litre, but Febi also do an equivalent for £8 a litre. I've never tried the Febi myself but having spoken to a few D2 guys in the US they use it all the time so I will be getting some for my next change.
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