Hi Salty, I think to some extent the answer to your Q depends on 'community standards,' and because of your concern about the liveaboard image I'd guess you want to be on the high side of that standard. The fact that you're asking suggests that you're aware that no one else in your marina has done something like this, maybe that is a singnal to you? If you're expecting to be one of the uglier or more cluttered locations - stop and think it through! I'd also ask: Is your marina one in which many people have personalized their slips, or is it pristine? Are you even permitted to attach things to the docks? If you're even remotely inconveniencing your neighbors by making them walk around your planned 'thingy' I think that's completely non-negotiable. I assume from your T-head location that you wouldn't be impacting anyone else's access. Second, even more than the dock is the boat itself - does it look clean and shippy and ready to sail?
If you're planning on cruising at some point, you and your son will have to be able to contain everything ABOARD, so you might as well start getting into that mindset early. Don't accumulate what you can't store. JMHO.