I learned so much along the way, including navigating the legal process needed to remove previous owners (squatters) who did not want to leave.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Just to make sure we’re both on the same page, I’m referring to the annualized total return that is included in the bigger pockets rental calculator — I wasn’t intending to compare RE to stocks, but maybe I’m missing something in your answer.  

This video is a great start and includes a lot of sample images (good and bad).

Some of those included those previously mentioned windows.  

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

I own 32 properties myself and have bought and sold over 300, including a few apartment complexes.

I'm looking to get their "package" which includes a Holding company, LLC Subsidiary​, Corporate Financial Program and an Estate Plan.

Listing your property there ensures visibility.Build Relationships: When agents reach out, respond quickly, highlight your property’s amenities, and showcase your flexibility to meet displaced families’ needs.Highlight Insurance-Friendly Features: Emphasize features like flexible lease terms, utilities included, and a fully furnished setup to attract insurance placements.This approach has helped me successfully market to insurance companies.

I would include your realtor in the conversation, at least when you're introducing yourself.