Hey, Lawler, I’m also in the tech industry and live in Melbourne.
FYI there are a number of good sailing schools in Melbourne that can teach you the basics and some can then continue up to
offshore or ocean qualifications.
If you’re going down the
training path, then I would look at the RYA schools rather than the Australian Sailing ones as AS really stops at the basic crew level.
(Disclaimer - I teach part-time at one of the RYA schools).
Once you’ve got some skills then look at chartering on the Gippsland Lakes.
Even a short (3-day?) charter will give you a feel for whether this is something you might be interested in doing more permanently.
Check whether they’re okay with taking your cats with you - I’d guess there will be some additional conditions around it.
There’s not really anyone in Melbourne doing
bareboat charters.
Also, if doing
training in Melbourne, make sure you do some of it in the middle of
winter so you don’t get the impression that it’s all fair winds and tropical sunsets!
Anyway, feel free to hit me up for more local info.
Chris