I am not a lawyer, here are my opinions:
1. All transfers of property are done by recording a deed.  You would be doing nothing different than a title company would do. So, if done properly, it should not create a cloud on title.
2. If you don't record the deed, there is no public record of the transfer.  You might be able to record it later, but this could raise a question, especially if you continue to operate the property under the previous owner.
3. Strictly speaking: yes.  Most lenders' paperwork specifies that a change of ownership has to be approved by the lender.
4. This is where most investors play.  Banks are usually happy as long as they get the payment.  But, I have had to refinance loans for investors when the loan was called.
5. An insurance policy is a contract between two parties.  If the property is sold to a new owner, the policy needs to be updated to reflect the new party. I think most insurance companies will simply update the policy since you are still the main person in the Trust.
I hope this helps,
  Neil Aggarwal
  Property Financing, LLC