I live in Honolulu currently but used to live in Tokyo (mother is Japanese) and still travel there on a regular basis (pre-Covid).

No, it is inside of an HOA neighborhood but the current regulations only restrict rentals under 30 days stays.

Over the years, however, we’ve found that we end up coming down to Orlando quite a lot, especially in the last couple of years, and we end up staying in vacation rentals (Reunion, Championsgate, Storey Lake typically).I would love to simply pull equity from the current property but given that it’s a long term rental and we are Canadians, from what we understand it’s not an option for us.we love reunion but I feel that would probably not be the best for ROI.  

I have 4 single family homes rented and rehabing 2 currently, in the pee dee area.

I am currently selling a 16-unit apartment complex, the first one to sell since 1998 when this buyer bought this one!

I am currently looking to invest in Augusta

We currently live in CA, but are moving to Illinois in the coming months - so this will be our state of residence soon.

If it's currently an STR they should be able to provide you with the p/l statement from prior years so you can see gross rents, operating expenses, average daily rates and occupancy levels.

Quote from @Andrew Steffens: I think going into an STR purchase with reasonable expectations of cashflow in this current market and rate environment is admirable. 

Currently, my partner owns 100% of the shares based on him putting 100% of the cash (let's say $1,000,000) into the property.