Now, I’m paying myself in the lower 5 figure range after product cost, marketing, employees, and reserves.Do I double down and open a new business in the same market, or play it safe and start investing the cash on hand?

A 3 bedroom with a garage in Aiea is a great product.  

Any type of investment real estate that you intend to fold for productive use qualifies for a 1031. 

It assures a quality experience for both the guest and us.We are at about 80/20 in favor of HomeAway/VRBO.

We all know it exists, but no one knows where to look, fewer even try, and only small minority ever get that lucky.I think the "you need a mentor" propaganda is propagated online by the gurus that want to sell you access to themselves or some other product or service that lines their pockets.Bottom line: Very few people give away anything for free.

Write letter to all the tenants reminding them that grease, hygiene products, etc should not be flushed or put down the drain. 

Ask yourself if the loan for that product type is normal for market conditions.

Matthew, you could always go and find a private loan to place in second position on the property, instead of a bank loan or HELOC product. 

If the masonry is too ugly, then paint the brick with the correct preparation and quality paint.

Finding properties on good streets in areas close to restaurants, retail and shopping, where you'll attract quality tenants is key.