I think the 110TSI would appeal to a broader customer base when time to resell comes, as not everyone wants a "sporty car" like the GTI or R and the lower price point would also be appealing to buyers. As you are already aware, the DSG transmissions on the lower spec Golf's is their achilles heel. Having your mechanic check the transmission is likely to be a waste of time and money as they wont be able to know how worn out the clutches already are and the condition of the oil or the mechatronics. It could fail 2 days after you buy it, or you might be lucky and it will run for 2 years without an issue. Personally I would avoid this transmission (especially if buying 2nd hand) as you may well be buying someone elses problem that they were sick of dealing with (eg they sold the car because of transmission issues which we see on this forum all the time).
But the GTI's and R's still appeal to a fairly wide audience, and being in Sydney you shouldnt have much trouble moving it on to a new owner when the time comes. I wish you were around 6 months ago when I had to sell my immaculate Mk7 GTI....its probably wrapped around a pole in South Sydney by now
The GTI's and R's are not only more enjoyable to drive and own in general, but they are more robust and reliable compared to the lower spec Golf's. So with that being said, I would recommend you find a nice GTI for between $25-30k.
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