re: Most challenging skill: parallel parking, stick or driving backwards with a trailer?

parallel parking a trailer with a stick is hardest

I'm proficient at all three but the most difficult of the three would be reversing a very short trailer. I grew up on my grandfather's rice farm and the most difficult thing on the farm to reverse was a rice cart. It's like reversing a 4 foot long trailer with a zero turn.

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Trailer

Those small ones can be the hardest depending on wheel base

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I rented a trencher from Home Depot recently... little short arse trailer pulling it with my Jeep. I looked like a damn fool trying to return that thing.

Parallel parking a trailer while driving a stick.

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Most challenging skill

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Posting pics on TD

I think the question results in a two-part answer. It is one thing to do each skill at a rudimentary level and another to master them.

I think both levels have parallel parking at the easiest but it does become more difficult as the car length comes closer to the space length.

I think backing a trailer is the hardest to do initially but driving a stick is more difficult to master. Even as the situation becomes more difficult both backing a trailer and parallel parking are things that can be approached slowly and methodically but mastering a stick is something that requires finesse and a very fast speed. While it will become muscle memory down-shifting with near-perfect rev-matching at speed (in a car that doesn't cheat for you) is mastered by very few people, in fact most people that drive stick have never even tried heel and toe shifting nor have they mastered power shifting or even clutchless shifting. For every person I have seen that can produce effortless heel and toe shifts there are ten that are just a money shift waiting to happen.

100% the trailer

I had no problem learning the first two; can’t say the same about maneuvering a trailer

Similar to the trailer is pushing out an airplane with a tug away from a gate onto the tarmac or active taxiway.

Easy to do with practice but difficult if process doesn’t get repeated

I fish. A lot.

Backing a trailer is probably the most challenging, but the smaller the trailer, the harder it is to back up. Backing a boat trailer is relatively easy due to the length. Backing up a little utility trailer or jet ski trailer is hard AF.