This is an extraordinary span of fecundity for one woman.  The usual maximum is about 23 years (age 20 to 43).  Are the younger children actually grandchildren?

Henry cannot have been born in Nov 1806 if Simon was born in Mar 1807.  If Henry was born Nov 1806, then he would have been age 43, not age 44, in the 1850 census, because the official enumeration date of the 1850 census is June 1st.  On several counts, it appears more likely Henry was born in Nov 1805.

1a.  D.L. Murray & N.R. Murray.  1995.  Marriage Index: IL, IN, KY, OH, TN, 1720-1926 (Broderbund CD-2):

Stroup, Michal

Walker, Mary

31 Mar 1803

Ross Co.

1b.  LDS.  Family Search: Internet Genealogy Service:  IGI - International Genealogical Index (online at FamilySearch.org):

Michael STROUP Spouse: Mary Ann WALKER Marriage: Mar 1803, Highland Co., Ohio Source: [patron submission]

Michael STROUP Spouse: Margaret A WALKER Marriage: Abt. 1826, <>, Highland, Ohio Source: [patron submission]

Based on the censuses, it would appear that Mary Ann and Margaret A. are the same person.

Henry STROUP Birth: 10 Nov 1806, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Simon STROUP Birth: 3 Mar 1808, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

These two births are only just nine months apart, which is hard to believe.  Yet, Simon could not have been born in 1807, just four months after Henry.  Nor could William have been born in 1909, less than two months before Claiborne.  The answer, I believe, is that this William is not the son of our subjects.  Based on the censuses, our subjects' son, William, was born in 1802/3.

William STROUP Birth: 8 Dec 1808, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Claburn STROUP Birth: 26 Jan 1810, Dodson Twp., Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Mary STROUP Birth: Abt. 1812, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Harriet STROUP Birth: Abt. 1814, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Margaret STROUP Birth: 20 Sep 1816, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Eliad STROUP— a mis-reading of Eliud Birth: 21 Mar 1818, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Cynthiana STROUP Birth: 6 Feb 1820, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Granville STROUP Birth: Abt. 1823, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Matilda STROUP Birth: 2 Feb 1839, Dodsonville, Highland, Ohio Death: 6 Dec 1854 Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

2 Feb 1839 is Matilda's death date; she was born ca. 29 Feb 1823 (see below)

Walker STROUP Birth: 11 Oct 1825, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Elma STROUP Birth: 22 Mar 1827, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Elizabeth J. STROUP Birth: 14 Feb 1830, Hillsboro, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

Margaret is too old to have birthed this child.  She was 49 in 1835! Nor does he appear in the 1840 census.

Wilber STROUP Birth:  Abt. 1835, Highland Co., Ohio Father: Michael STROUP; Mother: Mary Ann WALKER Source: [patron submission]

2.  Census Index:  U.S. Selected Counties, 1810 (Broderbund CD-313).  There was no Federal Census in 1810 in Ohio, except for Washington County.  On this CD, tax lists are substituted for some counties.•

1810 Tax List

Stroup, Michael

OH

Highland Co.

Newmarket

p. 7

3.  1820 Census Index and Digital Images (online at Ancestry.com; Image #2 of 2; extracted by Diana Gale Matthiesen):¤•

1820

OH

Highland Co.

Towne of New Market

p. 31

Ln. 6

Michael Stroup

131320-20010-0-007

These data indicate:

No. & Sex	Age Class	Therefore Born	Individuals Inferred
1 male	9 or under	1810-1820	= Eliud (b. 1818)
3 males	10-15	1804-1810	= Claiborne (b. 1810) = Simon (b. 1808) = Henry (b. 1806)
1 male	16-18	1801-1804	= William (b. 1802/3)
2 males	19-25*	1794-1801	= ? = ?
2 males	26-44	1775-1794	= Michael (b. 1779) = ?
2 females	9 or under	1810-1820	= Cynthiana (b. 1820) = Margaret (b. 1816)
1 female	26-44	1775-1794	= Mary
7	persons engaged in manufacture
*In the 1820 Census, the third column is age class 16-18 and the fourth column is age class 16-25; therefore, any individual in column three is duplicated in column four.  By subtracting the number in column three from the number in column four, you can create an age class "19-25."

Where are Harriet and Mary?  Are they deceased?  Or were they missed?  See 1830.  The older males may be kin or hired help.  There were only eight households in the entire town.  Also in New Market:  Daniel STROUP.

5.  1830 Census Index and Digital Images (online at Ancestry.com; Image #11 of 12; extracted by Diana Gale Matthiesen):¤•

1830

OH

Highland Co.

Salem [now Dodson] Twp.

p. 22

Ln. 1

Michael Stroup

011 030 010 - 321 100 100

These data indicate:

No. & Sex	Age Class	Therefore Born	Individuals Inferred
1 male	5-9	1820-1825	= Granville
1 male	10-14	1815-1820	= Eliud (b. 1818)
3 males	20-29	1800-1810	= Claiborne (b. 1810) = Simon (b. 1808) = Henry (b. 1806)
1 male	50-59	1770-1780	= Michael (b. 1779)
3 females	4 or under	1825-1830	= Elizabeth (b. 1830) = Mary (b. 1829/30) = Elma (b. 1827)
2 females	5-9	1820-1825	= Matilda (b. 1823) = Cynthiana (b. 1820)
1 female	10-14	1815-1820	= Margaret (b. 1816)
1 female	15-19	1810-1815	Either of these two? = Harriet (b. ca. 1814) = Mary (b. ca. 1812)
1 female	40-49	1780-1790	= Mary? Margaret? (b. 1785/6)

The problem with the girl age 15-19 is that she wasn't listed in 1820.  Is she not their daughter?  Or were the girls simply missed in 1820?  Listed next to Michael's brother, Anthony STROUP. 

6.  1840 Census Index and Digital Images (online at Ancestry.com; Image #5-6 of 10; extracted by Diana Gale Matthiesen):¤•

1840

OH

Highland Co.

Dodson Twp.

pp. 101B-102A

Ln. 8

Michael Stroup

001 000 001 - 021 000 010

010 000 - 000 000

0200000

These data indicate:

No. & Sex	Age Class	Therefore Born	Individuals Inferred
1 white male	10-14	1825-1830	= Walker (b. 1825)
1 white male	60-69	1770-1780	= Michael (b. 1779)
2 white females	5-9	1830-1835	= Daughter A = Elizabeth (b. 1830)
1 white female	10-14	1825-1830	= Mary (b. 1829/30)
1 white female	50-59	1780-1790	= Mary? Margaret? (b. 1785/6)
1 free colored male	10-23	1816-1830	= ?
2	persons employed in agriculture

7.  1850 Census Index/Images (online at Ancestry.com; Image #28 of 31):  District 14, Dodson Twp., Highland Co., OH, p. 279A, 977/977, enumerated 21 Aug 1850, official enumeration date 1 Jun 1850 (extracted by Diana Gale Matthiesen):¤•

Michael Stroup	71	M		Farmer	10500	Md
Margaret A  "	64	F				Pa
Mary A      "	20	F				O
Serena/Lerena Miller	11	F				"

Was her name really Margaret, not Mary?  Listed next door to John & Rebecca WALKER, on one side; and, on the other side, listed next to their son, Walker STROUP, who is nine households from their son, Henry STROUP. 

8.  1860 Census Every-Name-Index/Images (online at Ancestry.com, Image #15 of 57):  Lynchburg P.O., Dodson Twp., Highland Co., OH, Roll M653_986, p. 70B, PN 141, 1025/999, enumerated 19 Jun 1860, official enumeration date 1 Jun 1860 (extracted by Diana Gale Matthiesen):¤•

Mary Ann Stroupe	74	F		Farmer	13650	6000	Pa
Sarah Runion	23	F		Domestic			Ohio
James Shafer	35	M		Laborer			"

Listed five households from son, Walker STROUP.

9.  LDS.  Family Search: Internet Genealogy Service:  AF - Ancestral File (online at FamilySearch.org).

10.  WorldConnect / Ancestry World Trees (online at RootsWeb.com/Ancestry.com), including a file giving the following source:

Daniel Scott's book, History of the Early Settlement of Highland County, Ohio (compiled in 1890 from earlier newspaper articles) gives an interesting and lengthy account of the marriage in March, 1803 of Michael Stroup and "Polly" Walker in New Market (pages 81-82). Michael was a hat maker from PA who came to Highland county in 1801.  He carried an 18 gallon copper kettle on his head along with the tools and wool to make hats.  His brother, Anthony Stroup, also settled here.  This information is also found in History of Ross and Highland Counties, Ohio (1880), although neither mentions Simon.

11.  Email from Larry Stroup:

You have Matilda's birthdate listed as 2 Feb 1839.  I have been to the Stroup Cemetery in Dodsonville and have seen her grave stone.  It lists this date as the day she died, and her age as 15 years, 11 months, and 4 days.

12.  Birthdate calculated using Ben Buckner's Birthdate Calculator.

Name	Deathdate	Age at Death	Result
Matilda	2 Feb 1839	4d 11m 15y	29 Feb 1823
(Calculated birthdates should always be prefaced with "ca." — you can't be certain the person who calculated their age did it correctly.)