Some are more attractive than others for rental purposes, some encourage renters.  

Price would start at 1.1 million and go up from there.The zip codes in your spreadsheet that command the highest per night price are in the Kahala/Hawaii Kai/Portlock areas of Oahu.

I'm not a fan of vinyl cause it look cheap and I think if the place looks cheap then it attracts cheap tenants.

Small multi units in less attractive areas and conditions provide better revenue streams. 

When that gets mentioned it usually ***-u-mes that you've been networking diligently and have built up a stable of private lenders or connections to them, and/or that you have the savvy to be able to use hard money lenders safely and effectively.One philosophy is that if the deal is good enough to attract money partners and private lenders it has all the necessary financial "ingredients" to be profitable.

Those would fit with the modern feel, as well as attract eager buyers. 

Million dollar question...Do you really want to be an agent or do you really want to be an investor?

Its currently worth about 700,000 and a house would run us about 1 - 1.5 million (will likely take out a mortgage)What are your thoughts on keeping money in the NYC apartment vs liquidating it to pay off debt and invest in a home we will actually live in.And if we do sell - how can we avoid the 40K in taxes we will pay?

I live over in Norway so I can't exactly hop in my car and do a road trip of the place (which would probably be hard considering the millions of people and the traffic...

The entire premise of wholesaling is to get a property below market value so far that it is still attractive to an investor after you've taken your cut.