We have regular evictions at this scale and they typically will take a few months up to six or seven months if the tenant contest/hires an attorney.

They do a good job of regularly releasing episodes and they frequently talk about starting out with their initial capital pool and growing their business. 

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

Our mortgage brokerage works with real estate investors all across the country who face these same decisions regularly.

Trying to read between the lines it sounds like you have a regular owner occupied homeowners policy in place on a rental property. 

Pretty much any regular bank / lender is going to require themselves to be in first position on all the properties... so I don't think a HELOC type solution is going to work across multiple properties with multiple lenders.  

.: @Edward Toomey V and @Tyson Jones What I like about RentRedi is that they have a live webinar regularly.

After a few months you figure out that your team has not really engaged your property on a regular basis.

They claim it is a triplex (two regular units and an "efficiency unit".

Regular and transparent chitchats are the way to go.