I've also heard of requirements to own for at least one year before you can use the home as a STR.Hawaii is a leftist state that doesn't protect private property rights.

Quote from @Kyle Carter: What role does insurance play in protecting your investments.

Where is vacancy, maintenance/cap ex, asset protection, PM (include it even if self managing as you deserve to be compensated for your efforts), utilities, misc.  

The landlord should be named on the tenant's insurance policy for additional protection and to assist with tracking compliance.

It offers flexibility as a landlord to be able to offer more or less rooms as needed, protection to the landlord in that you can hedge with adding LTR or STR to the mix, and simplification to the business as your only dealing with one address.

Given when a return is audited some of these DIY firms note that (if audit protection is purchased) they will do a full engineered study to support the figures used within the audit.  

At the same time, they have heard from communities and citizens negatively impacted from STRs and want to "protect the sanctity and right of owners and residents" in their communities. 

Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal level Learn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are needed Know everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

Ensure you understand local regulations regarding permits; it’s usually a good idea for your associates to form an LLC for liability protection, but individuals can do renovations as long as they pull the necessary permits.

To simplify the existing lease I thought about asking the tenant if they would be ok modifying the addendums to get rid of the resident benefit package and the building protection plan.