I would both buy a property to get your feet wet and at the same time make a plan to scale.  

If you choose to move forward, I recommend having a backup plan in case Hawaii outright bans STR.

Beg family and friends to fund it for you.They "might" do it if they see you've learned a lot and your business plan sounds very solid.How do I know this "might" work?

I am beachfront (all 4 listings are in the same building, same floor, next door to each other), some are listed as beachfront, others aren't.  

Finally, check with the Town to make sure there are no municipal liens, Make sure they're on Town sewer, check with the tax assessor to see how many bedrooms the tax office thinks there are, (important if you are flipping) buy ok to have more bedrooms if you are planning to buy and hold.  

Explain your situation and see if there are payment plans or hardship programs available.The BiggerPockets forums have threads on tax liens and foreclosure prevention: https://www.biggerpockets.com/forums/41/topics/766025-surplus-funds-unpaid-taxes-in-foreclosure-saleAn experienced real estate attorney can advise you on your legal rights and explore potential solutions.Have you spoken with your local tax authority yet?

A complete overhaul of the kitchen and bathrooms, including cabinets, countertops, LVP flooring, electrical and plumbing fixtures.

A single-family home or small multi-unit property can be a great way to dip your toes in the water.Build a Team: Even if you’re planning to handle most things yourself, having a good real estate agent, property manager (if needed), and a reliable handyman can make life so much easier.Learn the Local Laws: Pensacola is pretty investor-friendly, but it’s always good to know local zoning laws and short-term rental regulations if you’re thinking about Airbnb or VRBO.Run the Numbers: Make sure you’re clear on the property’s cash flow potential.

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.