Should I buy a trainer or a cruiser?

[fursoc]

Hi everyone, if this has been answered before, my apologies, but I couldn't find it anywhere.

My family (2 adults + 2 kids aged 8, 10 when leaving) are in the early stages of planning a life of cruising starting 2018 or 2019 depending on how ready we are at the time.

I have very little experience in the water on a sailboat, and have never owned one. Obviously to do something of this nature requires quite a bit of experience to feel comfortable leaving the dock for good. Especially when kids are involved. I have signed up for some sailing lessons (competent crewing), but I can't see that giving me the experience I need.

What I feel we really need is as much time on the water as we can get. We would only be able to charter very occasionally with the costs involved, so the only solution I can see is to buy our own boat.

My question is; should I buy a trainer (~20-25ft), or should I be looking for our dream liveaboard cruiser (around ~35-40ft)?

Thanks,
Graham