These mostly consist of ocean front/view condos and homes.

My Google search revealed the principal of TruePoint started investing in 2020, and if that's true, this sponsor lacked all of the things that I consistently preach to look for--experience, track record, full-cycle experience, market cycle experience, and so on.  

Most people who are looking to pay for something that exists as networking online end up not using it and then complaining about.Whatever you pay for or don't pay for, if you try to meet the other people using it or at the meetup, and you do that consistently for six months, things will happen.

(Look up the biggest apartments or developments and see who sponsored/is sponsoring the project.)With the right people around you and consistent execution results are inevitable.Best of luck! 

some small collections, clean mortgage and 5 year payment history. Does this even exist?

If you are consistent with learning real estate over the next 4-6 months, you’ll be ready to purchase your first (or next) property in NO TIME!

I imagine the trend will land somewhere in the middle--maybe with an island or breakfast bar (or something new like a work-from-home "breakfast/desk"?) 

I’d recommend that you just be yourself around the tenants from other backgrounds than yours and focus on being consistent with them.

They can buy on another island or even the mainland.

If you are consistent with learning real estate over the next 4-6 months, you’ll be ready to purchase your first (or next) property in NO TIME!