If you're willing and able, I do recommend the "house hacking" strategy which is just a fancy name for buying a rental property and living in one of the units, because you'll get very favorable financing - an owner-occupied fixed-rate 30-year mortgage.I'd also say, analyze that property as if you won't live there and it's a pure rental, and make sure the property is still cash flow positive if there's a tenant in your unit because then you'll know if it's actually a good investment.And when you analyze it, include payment of a property manager in your #s because if you don't, and doing so would make it go cash flow negative, then you've just bought yourself a job because you literally can't step away from managing it without losing money.

There are so many options on how to approach this it gets overwhelming and i find myself moving on and always plan to "figure it out later"I have interviewed a few fiduciary advisors but have been very unimpressed thus far.   

You know how we do it?  

I know the prices of things are different on island compared to mainland so it’s nice knowing stuff like this.

Sometimes you need to know when you can hold em and when its time to fold em and move on.

You will learn how to manage investment property well while earning a solid paycheck.

Someone recommended a small lending company to get a mortgage for a buy and hold property. What should I do to make sure the company is trustworthy before working with them?

You never know what opportunities are going to come your way by going to your local real estate meet up.

Until you have $1 million or more in equity and really understand how to use an LLC, I recommend you just buy an umbrella insurance policy for $1 million.

I was just saying the same thing earlier on a reply to another post... if it works with rates where they are now, imagine how much better when rates drop, plus you didn't have to get it in a bidding war!