The lessons you learned the hard way in 2008 will be invaluable now, and it’s great that you’re aiming to stay small-scale and within your comfort zone of Sacramento, which gives you an advantage of knowledge in that market.Given your experience, I'd say start by focusing on three key areas to build confidence and minimize risks:Budget Control: Over-renovating was one of the big mistakes you mentioned.

In HI there are leasehold properties, cesspools, water catchment, and Lava Zones (on the Big Island). 

Zoning- certain towns are starting to restrict Airbnb type rental units.  

As a college student landlord you may have interaction with parents & if they find you unprofessional that may raise red flags, but if you have your s**t together you can ease those concerns.I am a big fan of college rentals.

I had two choices: stay in my comfort zone or take a leap of faith.

That would be the key element + no rental restrictions Ramsey,Do not forget there are a ton of REI properties in areas not close to the beach or in a flood zone in Florida. 

I would first suggest getting a real estate lawyer in that area.Is there zoning in that municipality?

Be careful with flood zone properties.

If so, no need for the red carpet or engagement photos, just focus on what they really care about: a great property, immaculately clean, and a seamless guest experience.It feels like you’re trying to cater to anyone and everyone, which can dilute your overall appeal.As for the garage games, many guests might actually prefer parking in the garage.

At a minimum,  you should understand what the current zoning is and what restrictions there are.As the post above mentioned reaching out or going in person to speak with the planning and zoning department will be very helpful.