There is no good investments, or bad investments.You as an investor need to decide what investing strategy works for you, define your criteria, understand if your criteria is possible in the market you are looking in, understand the risks/rewards of your critera, and then execute the purchase.While some agents are heavily knowledgeable about investments, most have zero clue.

You must clearly define roles and responsibilities while addressing all the what-if scenarios.

While I’ve been involved in much of the process, and I know Hawaii’s rules, regs and other intricacies well, I have never obtained investors, never signed contractsI and never opened escrow so I feel like I’ve been more of a spectator… I’m basically starting from scratch and I’m a bit nervous. 

Let me address your questions and provide additional clarity on key aspects:1.

Or are you managing every aspect on your own?

The automation aspect was cool, but as carriers are getting stricter it's going to be harder to have good delivery rates.

Throw in a dose of imposter syndrome and fatalism and you have a recipe for some mood swings right before a property is booked again.From a practical point, I would recommend great photos, a clearly defined target to whom you are advertising and understanding the best pricing of an area really well to ake sure you get booked in a timely fashion.From a more meta perspective, be aware that these listings don't typically get booked well in advance (families displaced by flood or fire, traveling nurses who need a new contract ASAP, and construction projects that realize they need a speciality engineer on-site RIGHT NOW don't book ahead). 

Welcome @Rebecca Morris,These are the 10 first steps I would recommend to get started in REI (real estate investing):1) Educate Yourself: Read books, take online courses, and attend seminars about real estate basics, market trends, and investment strategies.2) Set Clear Goals: Define what you want to achieve in real estate—whether it’s buying a home, investing in rental properties, or flipping houses.3) Choose Your Niche: Decide if you want to focus on residential, commercial, or industrial real estate, or perhaps a mix of these.4) Research the Market: Analyze your local real estate market.

@Mark Duttonjust to tackle one specific aspect of your portfolio - if you have 'mortgage payments' of $5500 and rental income of $6850 you absolutely do NOT have 'cash flow' of $1300 a month. 

If you’re 50 or older a defined benefit plan can allow you to contribute $250,000 + per year tax deferred.