However, you can still find multi fam in that price around the island and could potentially do an FHA if you're able to provide evidence that your employer lets you work remotely.

But, home prices are relatively high near me (Long Island, NY) and I know there are cheaper options elsewhere.

I'm also looking for any insights people are willing to share into Condo and SFH investing on Oahu.From the investigation I've done thus far it seems that across the island the median days on market is quite high by comparison to where I'm from in Sacramento or the national average.Oahu - 60 DaysHonolulu - 78.5 DaysNational - 34 DaysSacramento - 9 DaysEscrow/Closing times are 40-60 days which is much higher on the island than the mainland - my friend closed 21 days conventional on a house here in Sacramento last week.

I currently live in SoCal and own an STR in FL, and I'm very interested in the Big Island STR market.  

All the different islands have different rules and regulations.  

However, something to consider as a secondary option is Tybee Island.

Is investing in multiple island common ?

Those properties tend to sell at a bit of a premium, but with COVID bringing tourism on the island to record low levels, I'm noticing that more of these properties are starting to hit the market as people without adequate reserves are feeling the pinch. 

MTRs don't seem viable in pure tourism markets (lakes, ski towns, islands, etc) is there really sufficient demand for people who can stay 30 days?

Some big CapEx amounts that can add value are subsidized by Rhode Island, so you double dip in that you get a discount and might get a higher appraisal (or sale price) later.