Decent size umbrella policy? 

There's no one size fits all of course, but generally the STR/MTR/LTR mix in a multi-family unit can be challenging because the way renters utilize these properties is so different.

Lei, I'd be happy to serve you any way I can.For Ko'olina, I love the Beach Villas (as well as the entire Ko'olina area) and if you are primarily looking for a very quality property for you and your family to use, I'd recommend it.  

It felt like everyone I found were self-serving, looking to line their own pockets, or not willing guide because of fear of competition.

These are all STR communities that have similar amenities, close to Disney and have various sized homes that do well in the STR space. 

Along with a kiddy-pool sized litterbox in one corner of a room, cat urine and feces in the OTHER corner of the room on the carpet (newly installed by the seller when I bought), and a smell that made my eyes water walking in the front door.The lease has a clause for Tenant-Caused Damages resulting from tenant negligence.

Served a 3 day notice this past Monday. 

Depending on the size and how difficult it may be to get to it, I've paid about $5-8k.

Just not seeing any rents close to the property for 3/4 bedroom properties that would cash flow for a mortgage that size.

@Nick AmYou also may want to consider other matters besides taxes, such as state law requirements for management companies and serving as a property manager, especially with a tiered structure.