Open to any thoughts or suggestions.  

I would suggest you go on airbnb and look at homes that sleep 15 or more and look at some of what people have done with these homes to get an idea of what it takes, then look at their calendar, you'll see that they do well. 

Suggest you call the Housing Commission and speak with someone their - hopefully they answer/return your call.

Suggestions please?

If this is not the case, would you still recommend (as I suggested above) I start out in SFHs by renting out individual rooms on a 6-12 month long term basis?

Anybody have any other suggestions or experience with going the management route? 

It seems to have the highest fees for permits and STR’s in general but it’s the closest to all the major attractions.. do you have any tips and pointers to help me stand out or get started?

Any suggestions on what else I could do to rent them out? 

As @Bill Brandt suggested, go hire a 3rd party brokerage to handle it all. 

If you're planning on building an ADU or JADU 'yourself', my suggestion is to make sure you have some previous knowledge of construction and also make sure you know good sub-contractors in the following trades:  electrical, plumbing, foundation, roofing, framing, drywall/paint, stucco, tile, cabinetry, flooring, HVAC, concrete, etc.The last thing you want is poor quality work that has to be re-done because a handyman or the wrong tradesman did the work.