Now you understand that long leases are no hedge of protection for you they only benefit the tenant !

However, I don't like the use of insurance as the sole protection of your personal assets.

Yes, banks will finance such a deal in almost all cases, however, to protect their risk, they will underwrite it as if the taxes were paid to the purchase price (Or a %) even if they are reassessed much lower.

I am thinking of putting one my rental properties into a land trust plus LLC structure for privacy and asset protection.

If you really want to protect yourself, just partner with a family member and use their name on the LLC paperwork as the owner.

They're geared towards investors and offer huge opportunities to gain knowledge, ask questions, and network with other local investors. 

Get good contracts and LLC protection for that.

With this new agreement and forfeiting the deposit it doesn't sound like you were left with many, if any, protections or guarantees on how the property is returned. 

Instead of a $1,500 deposit up front, Tenant can opt to pay a monthly fee of $10 and Obligo will ensure protection of up to $1,500 for me as the Landlord.

I thought having title insurance and paying high lawyers fees offered some protection but apparently not!