Like Jake Baker suggested, keep good records and have a dedicated bank account for your property, properly separating personal and business expenses.

Personally I like the Section 8 program when the property is located in a super poor area with a ton of blight and crime.

You want this to be your backup plan if things take longer than anticipated, you do not want to dip into personal credit cards so i would use a heloc to help with down payment but try to keep a nice available balance on a heloc as your insurance policy. 

My personally favorite spot so far is Ko Olina but I'm open minded.

Real estate investing is forgiving; the average person can still make money even with some big mistakes.

And if you’re listing the house online, try platforms like LoopNet or local Facebook groups for real estate or community housing.Just make sure to do your homework and ask for references, check their track record, and make sure they’re following any local zoning or licensing rules.

Most are online, at civicsource.com  and happen once a month.

For my personal education, which one insurance should I have?

I agree with the person who said they are likely short of money and grasping at straws.

Quote from @Pixel Rogue: Personally, I think you are over-thinking this.