House hack on Oahu vs. long-distance multifamily?

[Mindi Rosser]

We've spent the last couple years following Set for Life and have stashed more than the 100K. We've been waiting for an opportune time to get into real estate investing and have done a good amount of education and focused on building a solid foundation. 

We are looking at our options for our first real estate investment. 

Since we live on Oahu, we'd ideally love to house hack here, but we're looking at million dollar properties being the norm for a duplex. There are some deals to be had (likely more in the next 6-9 months because the economy is tanking here), but it does not compare to the number of opportunities and returns that can more easily be found in Northwest Indiana. 

If we started in Northwest Indiana, we have the "hassle" of long distance investing. We have some trusted "boots on the ground" there already, but we expect there to be travel costs/time and other expenses to consider.

What would YOU recommend based on your experience? Open to opinions, ideas, suggestions - and questions we should be asking ourselves!