I would plan the addition to be "recessed" from the face of the building so the street appeal of the building would not be altered.

You need to protect your corporate veil by not co-mingling funds or using the LLC as an alter-ego. 

However, as your first capitalization and not doing it as a matter of practice in my layman's opinion isn't building a case of using the LLC as an alter-ego. 

A nonconforming use is a use of land, buildings, or structures that was lawfully established prior to the effective date of this ordinance, or any amendment thereto, but which does not conform to the regulations for the zoning classification in which it is located.Nonconforming uses may be continued subject to the following limitations:a) No nonconforming use shall be extended, expanded, enlarged, or moved to occupy a different or greater area of land, buildings or structures than was occupied by such use at the time it became nonconforming; provided, however, a nonconforming use may be extended throughout any parts of a building which were specifically designed and arranged for such use at the time it became nonconforming.b) No building or structure devoted to a nonconforming use shall be enlarged, extended, recon­structed, moved, or structurally altered unless such building or structure is thereafter devoted to a conforming use; provided, however, such building or structure may be enlarged or extended upon prior authorization from the Board of Adjustment, which authorization shall not be granted unless the Board of Adjustment makes each of the following findings of fact:1) The proposed enlargement or extension shall be de minimis in relation to the existing building or structure.2) The proposed enlargement or extension shall not increase the intensity of the nonconforming use, which is to say, it will not result in an increase in dwelling units for a residential use nor in gross floor area for a nonresidential use.3) The proposed enlargement or extension is designed so that it will not render the use of the property any less compatible than it is in its existing circumstances.4) The authorization of such proposed enlargement or extension is not otherwise contrary to the public health, safety or welfare.c) A nonconforming use of a structure may not be changed to another nonconforming use unless such change is authorized by the Board of Adjustment.

The "frankenstein" approach of moving Title to yourself to get the loan and then back just messes with your corporate veil since in my layman's opinion that is using the LLC as an alter-ego. 

I disagree with the town in that most agents and brokerages would want to disclose this as it can materially alter what you can do with the property.

Large expense that will come due real quick. 2) Roof 3) Foundation/slab But not a deal breaker, just be aware....most foundation issues are not a big deal. 4) Structural - alterations to load bearing walls, cut trusses in attic, etc 5) Electrical -  Is main panel adequate?

I would not pursue getting details on the physical alteration; you don't need it and you don't want to put yourself in a position that your failure to act on a verified incident could get you sued by those lovely neighbors in the future. 

Lastly, was this properly approved with the building department or has it been altered post-construction?  

But physically altering with infrastructure etc creates inventory and requires you to start a new clock to demonstrate your intent to hold for productive use and allow the 1031.