I am looking for a mentor to help me build a comprehensive plan that i can execute once I have the capital.

I know we had to provide our CA contractors license to even get coverage (we are doing two hotel projects here this year).

Well, you can, but not exactly what I was` saying, an LLC could be used in estate planning, assigning an interest or coverage could be an estate matter, the property doesn't have to be transferred into a trust or entity necessarily, but the basis for the activity can be for estate planning purposes. :)

It has no debt service coverage to begin with.

The property is actually on James Island and I was quoted over $2,200 for $150,000 coverage

Since it is likely your purchase is legal non-conforming with respect to current building codes, any insurance needs to covers reconstruction of the structure to current codes - some policies consider code-related improvements as enhancements to the existing building.I would also closely check the co-insurance provisions, loss of rents limits ($ and time), boiler coverage and general liability caps.A good commercial insurance broker can really help assess the specific risks and you may be able to loop in your other properties under the same general liability coverage if you consolidate with one carrier.

You get more coverage usually for a lower price, then add an addendum to your lease that permits you to act  as the agent of the tenant and purchase renter's insurance in their name to cover your property (if the tenant doesn't buy it).  

From NYTimes:Middle class renters getting priced out of some markets Nationally, half of all renters are now spending more than 30 percent of their income on housing, according to a comprehensive Harvard study, up from 38 percent of renters in 2000.

or do an Umbrella Policy for CYA.May want to weight out the extra coverage that an Umbrella Policy could offer in other areas vs. just do the LLC thing.LLCs and Umbrella can be double the protection

You may also need personal property coverage for furnishings.