I ordered a Freehand Pro and nylon gloves. What advice (apart from learning tricks and practicing) could you give for starting out in 5a?
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practice getting comfortable with letting go of your CounterWeight.
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Get comfortable with the basic throw/bind/catch before you get too focused on learning a trick. You’re going to hit your knuckles a lot before you get the hang of catching a yoyo with a counterweight properly. (At least that was my experience!)
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Everything @YoYoExpertGarrett said.
I love the freehand, but it is unforgiving to the knuckles (durable plastic for sure). Remember that the energy you send out will return. Walk before you run or you might pitch a beast that bites back😉
And grass or carpet are your friends. If you have a significant other don’t play near them. Someone may get hurt or at the very least be super annoyed with the sound of drops ( but my wife loves it, duh)
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if you drop it, and it rolls off the carpet, and you can’t get the yoyo, just step on the CounterWeight. 
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Bandaged knuckles are temporary, but 5a glory is forever!
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Avoid throwing near storm drains and doing aerial tricks beneath trees
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There’s a cheap Duncan counterweight set that has a soft rubber counterweight that I used for a bit until I felt comfortable tossing it and catching it. Helped to not bust my hands up with plastic!
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How do I get my string length right? It always seems way too long. And I also can’t seem to catch it without painful contact with my middle finger.
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I play 5a with a shorter string than 1a , but not as short as 0a. Usually from the yoyo at the floor the counterweight is between my belt and my belly button.
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