To answer your question - yes, you will need an attorney who will represent you in this and make sure that you have the right language and protection in the docs but he will not tell you if it’s a “good deal” or not. 

@Jarod RotoloIt sounds like they are just trying to protect their family member.

These folks will be responsible for protecting your asset physically and financially so taking your time to deep-dive into some research before making any moves will increase your chances of success when you're out-of-state - it is not impossible!

After I posted this I spoke with two real estate attorneys AND my accountant who confirmed what the two of you said and added some points: The  LLC adds a layer of protection, one attorney did bring up that an LLC does not protect the landlord against liability for lead paint (the vast majority of homes here are pre-1978).

@Guy YoesHaving your management company the owner of the property weaken your asset protection.

What kinds of things do you do to protect yourself on a house with a pool that is a long term rental?

The commercial liability (or umbrella policy if you have less than 4 properties) is the overarching policy that coordinates gaps in all other insurance policy to give you greater protection.  

Make sure you are only choosing based on approval criteria and not any protected classes.

Aloha @David Dong,   I would contact the Hawaii DCCA - Consumer Protection Office at eight o eight five eight six two six three four to get some guidance and ensure you don't violate any Hawaii Laws in securing your property and handling the tenants deposit. 

I don't know what I need to do to legally protect myself and I certainly don't want to be in a potential squatter situation.