My wife and I have 4 long-term rental units and looking for a better way to manage/track expenses/income.

I'm thinking one might be that it wouldn't show established long-term tenancy in the case that I may want/need to for lending purposes. 

I have worked in long-term care for over 20 years now as an Administrator , and now I am running a healthcare consulting business on the side. 

Your list looks good but as others mentioned it doesn't hurt to think long term and explore refi options as well.

And then I didn't call for a long time while we tried to manage out of state for the first year.

Its about 80% occupied by insurance relocation tenants and I’m currently getting 3 times long term rent

I have a particular interest in islands, as my long-term goal is to captain a catamaran and offer tours for snorkeling, sunset cruises, etc.I'm interested in places that offer great ROI without being overly expensive.

Particularly if you owned the property for a long time, much of the capital gain is due to inflation and should not be taxes.David KrulacBigger Pockets Podcast #82

I could get more by expanding before getting into it, which will be more beneficial in the long run.

However, clarifying the long-term business objectives/strategy is key before finalizing your entity set-up.