The area is great, but as @Noah Laker said, you will have issues with townhomes in many area in terms of doing short-term there.

He will frequently frame things in terms of a trade off.

You need to think about your investment in terms of ROI (Return on investment).  

I am out of state so I have a reputable PM handling the tenant but I want to make sure I am adequately protected in terms of liability and such.

When you pull out the 75% value (which in your example is $150k) and use that to pay off your initial $100k investment and $50k renovation costs, you’re breaking even in terms of cash.

And if you provide more information maybe folks on here that are familiar with the market can help you in terms of renting vs. selling.  

The next individual plan (49) seems more reasonable in terms of "actions".

His approach was straight to the point in terms of making sure we were on the same page business wise considering everything going on currently, but overall was a very informative & positive call...I’m really looking forward to getting started.

It worked, I got a few deals that way after awhile, but there are more efficient ways to market if you have more capital to work with like PPC or hiring VAs for lead generation.I'd still advise that if you're just getting into business, I would start slowly in terms of marketing spend.

.- Hawaii property tax and insurance is considerably "okay"- Each Florida city has its own different trajectory in terms of appreciation, but HI appreciation depends on island and the town.- With most job now is being done remotely, especially in tech, Hawaii is becoming a viable choice.- However, the thing that makes Hawaii very doable is that the cost of flying is cheap, from CA one way the cost is $90-$200 depending on the season. - Every Hawaiian Island is very different from one to another, and between towns is also a bit different.