DIY possible or is there a specialist I can engage? 

Consider focusing on the main objective of house hacking which is to get other people to pay for your living expenses.

Further, you should add the LLC as an additional insured if you do not have separate coverage.If the object of this exercise is to less the # of claims you have on your properties it would pay to look at what the insurance companies look for when they inspect:1. cracked or broken driveways or sidwalks2.

broaden the marketing a bit...occupational therapists, physical therapists, resperatory specialists and on and on...they have outsourced all these formerly doctor functions to specific professionals now, and like traveling nurses they are often young, getting paid well and love to travel.

I would also read this book, Florida Foreclosure Sales: How to become and stay wealthy by mastering objections, marketability, and possession by Natalia Oulette Grice.

In your case, asking to see examples of property listings they had showing for lease then using something like zillow's historical lease information to see how often they are really available for lease could have given you a little more objective information about lease lengths.

@Tyler SpeelmanNot an ira custodian or specialist and I have heard two opinions on this.

In fact, we even had a realtor/design specialist coming in to evaluate the house.

Personally I would recommend sticking with free or mostly free strategies when starting out, as it will take you time to learn the business, the objections/situations you will face from potential clients, and so much more.

Steven Pinker (a well known and highly respected cognitive psychologist) talks and writes about how--by many objective measures--life is much better for most people today than in previous generations.