Remember the emotional side of things from the seller/landowner perspective.  

I have learned this lesson as I got deeper and deeper into Real Estate...

Then you can take a deeper look into that strategy to make sure.

I'm willing to take my time to find the right fit, and luckily I have a bit of a hometown advantage since I grew up here and have friends who are realtors who can help advise me as I delve deeper and run numbers.

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.