STOP READING BOOKS, get to your local RE meet up, 

I just renovated a 2 BR / 2 BA single family built in 1900 and it was 55K.Also, there's no such thing as "ARV 200-300K" - you need to conservatively estimate the ARV and come up with a much narrower range.Finally - are you local?  

I'm particularly focused on local STVR (Short term vacation rental) properties that are officially licensed by the county of Hawaii to operate short term rentals.

Near outdoor activities, good food and some kind of water.

I also found a small local community credit union who will write first position HELOCs.  

:)I would recommend to checkout your local meetups in your city.

I recommend you print, study, and highlight the HUD guide: https://www.hud.gov/sites/dfiles/PA/documents/HUDAsstAnimalN...You should also check with a local HUD office to see if they have any additional guidance they can provide you.Keep in mind, not everyone is subject to Fair Housing requirements and you may be exempt from allowing the ESA! 

You will probably want to hire a local engineer to help develop the site plan.

Building a strong local network of trustworthy professionals is incredibly helpful as you get approved for financing and start property searching.

There's real logic in living on a local golf course if an integral part of what you do in the community is sell yourself as a successful person.But I think that for most of the people on that golf course, there are deeper, less healthy reasons to do as they do.