Will the real James Skaggs please stand up? James, father of the Long Hunters

There are many genealogical records available from the 1700s for James Skaggs, making him appear to have been everywhere at all times.  I want to try to take advantage of years of genealogical research by many Skaggs researchers to separate these James from each other:

1. James and Rachel Skaggs - the parents of the Long Hunters
2. James, Jr. and Mary Skaggs - the Longhunter James, son of James and Rachel
3. James and Susanna Scaggs - lived side-by-side with the Long Hunters in Virginia, then went west and ended up in Warren County, Kentucky
4. James C. Skaggs – Revolutionary War pensioner from South Carolina
5. James Scaggs and Catherine Reaser/Mary Brinker - lived with first wife Catherine Reaser in Spotsylvania County, Virginia, then with second wife Mary Brinker in Frederick County, Virginia and the Chew's Folly farm in Prince George's County, Maryland

First, let's discuss James and Rachel Skaggs, the parents of the famous Skaggs Long Hunters.

1. James and Rachel Skaggs:

This couple was the James and Rachel Skaggs who were parents of the Longhunters.

1745 Lyman Chalkley, Chronicles of the Scotch-Irish Settlement in Virginia Extracted from the Original Court Records of Augusta County 1745-1800, Volume 1

Augusta County Court Records. Order Book No. XXIV.
page 431
Humberstone Lyon deposeth that James Conoly said Humberstone Lyon stole fifteen red deer skins and also twenty-eight red deer skins which Conoly had left at the house of JAMES SCAGGS. Also deposition by Samuel Stolucher, the same. Also deposition by Erwin Patterson.

1746 Nov. 19, Augusta County, Va. Settelment South West of Roanoke become important, four roads to be built, 2nd road was ordered from Adam Harman's on New River to North Branch of Roanoke, with workers including James Skaggs Virginia Historical Magazine Vol. 30, page 195

1749 July 1 Lyman Chalkley, Chronicles of the Scotch-Irish Settlement in Virginia Extracted from the Original Court Records of Augusta County 1745-1800, Volume 3
Abstracts of Wills of Augusta County, Virginia. Augusta County Court.
Will Book No. 1.
page 18
Page 276

John Elswick's appraisement, by Thomas Ingliss, JAMES SCAGGS, Ebenezer Westcoat.

1751 May 28, James Skaggs received 100 acres on Little River of Woods River from Francis Riley Deed Book 3, page 226

1758 Feb. 17 Lyman Chalkley, Chronicles of the Scotch-Irish Settlement in Virginia Extracted from the Original Court Records of Augusta County 1745-1800, Volume 3
Abstracts of Wills of Augusta County, Virginia. Augusta County Court.
Will Book No. 3.
Page 202

Colonel James Patton's estate; appraised by Thomas Stewart, John Ramsey, Edward Hall. List of bonds, bills, &c., due the estate: [from a lengthy list that includes] JAMES SCAGGS, 12th February, 1753.

After Colonel James Patton was murdered by the Indians at the Draper's Meadows Massacre, his estate was due payments from settlers, including James Scaggs, to whom he sold property as part of his real estate development scheme.

1754 Jan. 11, James Skaggs received 104 acres patented to Samuel Ratliff from Daniel Ratliff, Deed Book 6, page 100

1769 Apr. 26 Chronicles of the Scotch-Irish Settlement in Virginia Extracted from the Original Court Records of Augusta County 1745-1800

Deed Book No. 16.

Page 49

JAMES ( ) SCAGGS (SKEGGS), Sr., and RACHEL ( ) to JAMES SCAGGS, Jr., £100, 104 acres patented to Samuel Ratlive 22d August, 1753, and conveyed to JAMES, Sr., on Meadow Creek, a branch of New River. Teste: William Preston, Richard Whitt, James ( ) Skggs, John ( ) Skggs, Is. Christian, James Buchanan, W. Ingles.

The above is an important deed since it shows James Skaggs, Sr. as grantor, James Jr. as grantee and another James Skaggs as a witness.  I will refer to this record again when discussing the other James Skaggs.

1773 Mar. 2, James Skaggs and wife Rachael sold to John Plickinstarver 78 acres for 40 £ land on the Medow Creek of New River, Fincastle Co.

1773 Oct. 26, James Skaggs and wife Rachael sold to Thomas Maston 78 acres on Medow Creek, New River, Fincastle Co.

1776. Fincastle Co., VA. "In 1776 the Committee of Safety for Fincastle County recorded that Captain JAMES SKAGGS was unable to serve any longer because of his infirm state of health, and Thomas INGLES was appointed to succeed him. Presumbaly this is James SKAGGS, Sr." --Harwell, Committee of Safety, 76, in Kegley, Early Adventurers, 367.

1778 Apr. 6, James Skaggs got 68 acres on Medow Creek a Branch of the New River in Montgomery County from the executor of John Buchannan's estate

1779 James Skaggs Sr. is court for a suit against Peter Raffle

1779 June 1, James Skaggs sold to Richard Whitt 68 acres for 280 £ on Meadow Creek branch of New River

1781 Sep. 14 Montgomery Co., VA. According to a certificate from the Commissioners dated 1781, RACHEL SKAGGS had a tract of 150 acres surveyed in her name. --Kegley, Early Adventurers, 367.

1784 Montgomery Co., VA - Survey for Rachel Skaggs 14 Sept. 1781, written on survey was: Platt given up and transferred to Henry Skaggs, May 1784, 150 acres land by virtue on an entry on a certificate from the Commissioner of the District of Washington and Montgomery Counties for 400 acres lying in Montgomery County on Little River a branch of New River (it goes on to describe the land by its boundaries)

The June 1, 1779 deed with James Skaggs as grantor and Richard Whitt as grantee combined with the 1781 land survey for Rachel Skaggs indicates that James Skaggs Sr. died sometime between June 1779 and September 1781.