Since it isn't a canister filter, it will drip when removed either from the filter, or the hoses leading to the filter, so you will end up with oil on the bottom shield. Since it has/had sound deadening material, that will likely soak some of the oil up, but then you'll be driving around with an oil soaked panel. When it rains, it may cause the oil to come out, and drip around.
Far too messy to try from the top, and you'll end up with a mess to carry around until, well probably forever, or when you replace the bottom shield.
There weren't a lot of sizes for spin on filters, the TDI is about the same size as most of the GM spin on filters from the 90's, all are about 3" diameter, so it's really not all that big, except when compared to the newer cartridge filters in the ALH and later models. It's actually kinda small compared to the V10 oil filter.