What Brand and color paint would you guys suggest?

That will allow you to build the additional legal space further amplifying the value of the proprety (more HELOC money). 

@Ketch BaysStarting small in a cash-flowing market is a smart way to gain experience and build confidence without overextending yourself financially.

I feel like this gives me an instant screenshot of every expense for each building so I know Building A paid $1800 for insurance, Building B paid $2100 for insurance and Building C paid $2400 for insurance as opposed to having one account and seeing Insurance was $6300.

It's actually the best strategy in the Nashville area if you can build an HPR yourself and own both, STR the other side. 

I was on island earlier in the month for an eviction trial and stayed at the Waikiki Banyan for a few nights - that seems to be a popular STR building.

The local investors will need to know their local real estate and rental markets and depending on the infrastructure the investor has in place or is willing and able to build, that will dictate how much time and effort they would need to contribute.

For example, it is not unusual for me and my business partner to buy 4-unit buildings for about $250k and be able to rent them out for $4,000+/mo. 

For C to B-Larger developments announced nearby-Increased activity in new construction-Building of commercial retail in or near the neighborhood. 

Quote from @Theresa Holl: Quote from @Varinder Saini: We are building a real estate AI platform that specializes in analyzing disclosure packets of hundreds of pages and generating concise single report of important findings.