mnmlikereal
As someone who almost returned the handy - because it was far too complicated to use while getting setup and holding onto it and adjusting your vr headset, etc., the following works pretty well.
Handy is connected to small monitor stand (just the base and pole of the stand) using these:
https://www.amazon.ca/gp/product/B08PK7ZXBX
https://www.amazon.ca/gp/product/B0030HO6SM
https://www.amazon.ca/gp/product/B005KWPJ04
https://www.amazon.ca/gp/product/B00JQNRTDI
https://www.amazon.ca/gp/product/B0030HO6SM
https://www.amazon.ca/gp/product/B097BG9Q9F
Even without the hands free part, the following should still work, i.e you could have the sleeve in the handy without the user being present or hard.
Setup the strap and sleeve ahead of time, i.e. you are not involved so no need to be ready.
To keep the handy gen2 sleeve in place on its own, I use a very soft flexible/stretchable rubber ring (RingO2 C-Ring with Ball Sling) plus a small piece of soft packing foam, this is just the right size to go around the outside of the handy sleeve to create a larger lip on the sleeve, and prevent the sleeve from falling down and out of the 3rd party velcro based strap I use, and flexible enough you don't feel it. This lets you keep the velcro strap very loose (my preference), holds the sleeve in place regardless of user presence or erectness, makes setup super easy (no need to be erect, or lubed, etc.), after use you don't even need to undo the strap, you can just leave it in place. This setup has never had the sleeve come out, or the velcro come loose.
The other thing I use is a small microfibre towel with a hole cut in the middle and placed between you and the sleeve, catches 99% of any lube or anything else that leaks out and keeps your dangling bits away from the handy.