However, Hawaii appeals to people from around the world and now that many high income earners have the ability to work virtually, there is even greater interest in Hawaii housing than in the past.  

For example, greater Gatlinburg has a pretty robust infrastructure for STR, which can make startup easier, but the market doesn't appeal to every tourist that wants to visit our region.

Also, the idea of continuing to pay this thing off faster has some appeal as I approach retirement in 4-5 years.

How can I best approach the broker/sellers to make an offer appealing to them?

Despite these built in challenges, the curb appeal was fantastic and the interior was charming.

The cities you've listed vary wildly in features and appeal.

.- As long as I can sell myself to the seller, I could be an appealing option since I have strong job stability and financials.

A front porch is nice if you are on a street with nice curb appeal or a cool vibe of some sort where its fun the sit back and watch the world go by Super clutch if it's on a parade or event route. 

Looking to add a bathroom or two to my home for that ARV and increased rent appeal.

We did a small cosmetic renovation which helped boost our appeal to the STR market.