You have to weigh the benefit of the insurance claim payment versus potentially having your carrier cancel you and perhaps get black-balled by the insurance industry.

Since the trust is a disregarded entity, the benefit is bypassing  probate, not tax issues or liability concerns. 

I do like the tax benefits and leverage.

Longer Tenure in HomesData from the National Association of Realtors (NAR) shows people are staying in their homes for a decade (see graph below):This increased tenure means homeowners benefit even more from home values growing over time.

If you’re comfortable with a bigger investment, a duplex is good for the benefit of additional cash flow and you could house-hack.

While an LLC can offer liability protection and tax benefits, it’s not essential for a single property—personal liability insurance and an umbrella policy may suffice for now.

It will familiarize you with the basic terminology and benefits.

How much weight do you give to the cash flow benefit of cheap debt when the property is priced above market?

Separately, the benefits and disadvantages of renting to Section 8 is a topic of extended debate on this forum.

I don't believe sellers should benefit from any tax savings.