Make sure you do your numbers before buying, avoid emotional purchases....Check out my blog on Rentals in Hawaiihttps://www.biggerpockets.com/blogs/8050/48883-buy-a-hawaii-vacation-rental-and-have-it-pay-for-itself-unicorn-alert

If this is more of a blanket loan then rates can be all over the place, but you'd still be looking at a 5 or 10 year term with a 30 year amortization.Ideally, you'd want this to be a multifamily loan as the lending pool is deeper and the terms tend to be better compared to a blanket loan or residential properties funded as a commercial loan.

He is totally compartmentalized and makes decisions which are sometimes very cold with zero emotion.

First take a look at The Ultimate Beginners Guide https://www.biggerpockets.com/real-estate-investingOnce you have a better idea of the strategy you want to use to invest in real estate you can dive in deeper to build up a good foundation of basic knowledge in that area.

Do not ever get emotionally involved.

Granted, this is somewhat an emotional choice because I like the area.

Then if they aggressively counter you can look deeper into the numbers and tell them the max you can offer. 

Base your decision off the numbers, no emotions :) Best of luck!

Emotions, misdirected compassion, anything that interferes with making the right financial decision is indication you are operating as a hobby.

Just run your numbers on the conservative side and don't bring emotion into the deal.