For example in city of San Diego you can designate a few units as affordable units and build 15 units in a single family zoned area.

Agree that amount looks very small another option, not sure what your goal is, but if you are looking to purchase some down the road, change up your strategy and maybe do a personal line of credit for now.

I've struggled to find deals where a positive cash-on-cash return would be possible or even breakeven.Expert advice neededI am curious to hear from other investors what types of house hacking strategies has worked in Hawaii (or similar markets). 

Just run search on Residential to create a fairly good-sized list of active listings, then look for the Realtor designation, or lack there-of, then note the brokerage name and contact info and contact them directly.If you are not concerned about discount CE credits, using certain features like RPR, or becoming a GRI, etc., then my guess is you will save a fair amount of money (my annual board fees were $620). 

I figured asking would be the best strategy but definitely wanted to have some ranges like you mentioned prior to sounding completely ignorant.

My STR was designed to appeal to a large audience so I can't speak to the STR market but I suspect that it is not all that different from the MTR market.

I don't lend in NY (we do investor loans in most of the country and consumer loans only in FL, but we do nothing in NY), so I don't have a dog in the hunt here, but don't discount other types of loans, including a loan designed specifically for flipping.

Greetings, i am a 20 year old college student at Massachusetts College of Art and Design currently living at school in Boston.

I’m very intrigued by the service and how detailed the protection strategy is.

I am interested in flipping houses and rentals but am also open to other strategies as my knowledge and experience increase.