Any specific neighborhoods within the region to look into? 

Agreed,Lot's of deals to be found in Ohio.Tougher nowadays but still enough to stay busy.Just to answer the OP's initial question also.Loosing on a deal in the first few years is risky business.When I first started investing in 2010 and back home in Australia, I built a large portfolio and fairly quickly.Lot's of debt...Monthly mortgages where costing me more than I was generating in income.It was a slow bleed so I decided to liquidate and move to cashflow friendly markets in the US (Specifically Ohio).In hindsight, those same properties if owned today would have made me millions in capital gain profits.So if you are looking for an appreciation play, make sure to have enough income from your W2 or other means to withstand the slow monthly bleed until the properties appreciate so much that you end up being in the green even tho you bled monthly.Again, very risky business IMO.Much success

Do you have specific areas on Kauai or Maui in mind?  

But, that is not always the right answer and you should speak with someone familiar with your personal situation to get advice specific to you.I'm not sure where in CA you are located, but I have several referrals in the San Diego area if you're interested.

Many jurisdictions have established laws that the person wholesaling or assigning the contract must be a licensed Realtor (Illinois specifically). 

If you have any specific questions on the market feel free to ask and I'll do my best to answer or point you in the right direction.  

Of course I will hire a property manager Cleveland, Ohio is a great market to focus on for cash flow and specific pockets have gone up 2x and upwards of 4x in the last 5-10 years even!

Grow and raise a lot of our own food.

RetiredMD offers a great program for this and good courses and community for you to share specific details on.

If not I will see if I can find one to chime in.There could be other specific circumstances that cause a taxable event, but in general this is the strategy and I have seen it work well.