I haven't found many details about the family during the ten years that passed from Andrew's death until Sarah moved to Iowa. But there are bits of information here and there.
Source [1], Dr. Van Sickle's Book, page 193, section #8.
"... Sarah was a doctress (mid-wife) and a successful practioner."
Source [4], Zilla and Ila Manuscript, page 29, para 99.
"Our great grandmother, Sarah Courtright, Van Sickle became a midwife after she was widowed in 1821. With twelve accouchments of her own, she must have been well qualified for the time and place. She rode horseback to her cases and was engaged well ahead of time. She was continuously occupied for many years. Her fee of $25.00 was just for the delivery, an extraordinarily high charge for those days. Grandma (Ann Drusilla) had to be cared for in various neighboring households during the times that her mother was occupied."  
Source [4] Zilla and Ila Manuscript, page 5, para 18.
"Grandma (Ann Drusilla) ... told me when I was a small child that she had gone to school just three months. And she must have been eleven or twelve* at that time. Old enough to have been the butt of improper attention from the big boys who made up most of the student body. Some such incident apparently caused her removal from school. As we know, however, she somehow learned to read and write and in her old age was an avid reader."
(My note: *since we don't know her age at the time of her schooling, we don't know whether this happened in Indiana, Illinois, or Iowa. 
1827, five years after Andrew's death.
Sarah, now about 43, saw many changes take place in her household in the first five years after Andrew died. Her family was growing up and her older children were seeking their own fortunes.
In 1827:
Thomas was 24
Jacob, 22
Martin, 21
Hannah, 19
Eliza, 17
Almira, 15
Moses E, 12
De Witt Clinton, 11
Sarah Ann, 9
Ursula, 7
Ann Drusilla, 5
Stories about fortunes being made in the lead mining district of northern Illinois and the Wisconsin territory lured many men to pack up and leave home. The Van Sickles' were no exception. Some of the family went to the lead mine district by 1827 - we don't know how many went at that time but De Witt Clinton Van Sickle wrote for Dr. Van Sickle's book para #35. "... In the autumn of 1827, he went to the lead mines in Jo Daviess County, Illinois (the present site of Galena), where he went to mining, and was successful ... ." (My note: I find it hard to believe that De Witt Clinton went alone to the lead mines at eleven years of age in 1827. We are told that others of the family went to the area before Iowa opened for settlers in 1833. We can only imagine who (if anyone) might have gone to the lead mines with De Witt Clinton in or before 1827 but we know from Dr. Van Sickle's book that Hannah was married at White Oak Springs, Wisconsin, on October 1, 1828 and Eliza was married at Galina, Jo Daviess County, Illinois, to Alexander Simpson before the lead mine census of 1830 was done (they appear in that census). It seems to me that all the older children had moved to the lead mine district in advance of Sarah's bringing the younger children: Sarah Ann, Ursula, and Ann Drusilla.     
Continuing with Dr. Van Sickle's book and De Witt Clinton, para #35. " ... after remaining there awhile (Galina), he sold out and went to the lead mines in Iowa (the present site of Dubuque), where he also found the mining business profitable, but was soon driven away by hostile Indians. He served as second Sergeant in the Black Hawk War of 1832, in which he was wounded, and narrowly escaped death by having his horse shot under him. (My note: he would have been about 17.) "At the close of the war he went to Muscada*, Wisconsin, where he, with others, built a furnace for smelting lead ore; from thence he went to Clayton County, Iowa (which was then in possession of the Indians), where he kept an Indian trading-house ... ." (My note: *Muscoda; originally named English Prairie. There was only one smelting furnace built at Muscoda, and according to later accounts, it was doomed to failure from the beginning. While it was located on the Wisconsin River where shipping was convenient, it was located too far from the actual mining activities to make it convenient to miners. If anyone made any money from the venture, I imagine it was the most influential partner: Col. William S. Hamilton. 

I've wondered how many of theVan Sickle boys were using their mother's money to finance their quest for lead fortunes?

Source: [4] Zilla and Ila manuscript page 4 para 16: "I heard remarks during my childhood about Sara (Courtwright) ... having been so injudicious as to let "those boys waste" the estate, which consisted mostly of land. Apparently all the boys took to the frontier"

Was the Muscoda venture costly not only to De Witt Clinton, but was his part financed by Sarah? Did the "wasting" of Sarah's estate cause friction in the family? We know that after Iowa opened to settlers, De Witt Clinton lived  in Clayton County, Ann Drusilla lived in Clayton County, and their mother Sarah lived in Clayton County - and Sarah had members of both the Courtright and Van Sickle families living in her home (1850 Census). But Dr. Van Sickle's book does not mention Sarah's household.

Assuming that De Witt Clinton was the only one of the Clayton County family  who answered the call from Dr. Van Sickle for family information to include in his book, why did De Witt Clinton include Ann Drusilla's family and not Sarah's family? Was it because De Witt Clinton 
and his mother were not on speaking terms? Pure speculation on my part - but interesting. 

From:       http://www.wisconsinhistory.org/turningpoints/tp-026/?action=more_essay
.By 1829, more than 4,000 miners worked in southwestern Wisconsin, producing 13 million pounds of lead a year.

From:       http://www.rootsweb.com/~iljodavi/census/Intro.htm
"In the rush to get rich, family members spread out over the entire Lead Mine Region. The first miners worked around Galena, Illinois, in Jo Daviess County, working north into Grant, Iowa, and LaFayette Counties, Wisconsin. The Dubuque County, Iowa, lands were not available to American miners until 1833 as designated in the Blackhawk War Treaty. Families split to claim the rich mines or to open a branch store unconcerned with state or county boundaries."

From:      http://www.iowacountyhistoricalsociety.org/links.php
Miners who moved to the area in the 1820s and 1830s wasted little time in constructing shelters. Some simply burrowed holes into hillsides, earning miners the nickname "badgers." The tools and techniques involved in lead mining in these early years were relatively simple and inexpensive, allowing lucky miners to strike it rich with little personal expense.

Lead Mining
(My note: don't confuse Iowa County, Wisconsin with the State of Iowa, site of Dubuque. 

Source: The Milwaukee Sentinel, October 10, 1920. Muscoda - on the Wisconsin River.
"The way in which the village was begun, by erection of a smelting furnace, is rather stunning, in view of the absence of lead in the region adjacent," says Joseph Schafer, Secretary of the Wisconsin State Historical Society, discussing the history of Muscoda. "The motives of Col. William S. Hamilton of Wiota to build a furnace at English Prairie can only be conjectured."

"... In the year 1836-'37 the price of lead declined so alarmingly that little of it was made and the smelters had nearly all ceased to operate." 

Some of the adventurers who came in the expectation of acquiring sudden wealth were doomed to disappointment. There were some who sought to avoid the rigors of the northern winter by coming in the spring and returning to their genial southern climate when snow began to fly. These tenderfeet were denominated "suckers" by the hardier miners, an appellation that was later transferred to the state of Illinois. Their superficial workings were called "sucker holes."

Page 03.
Page 03.

The widow Sarah in Indiana 1822 to 1832.

Sarah Courtright Van Sickle Redmond
         A Northeast Iowa Pioneer
This "wasting of the estate by the boys" must have been a volatile issue within the family - it was still being discussed by grandma Ann 60 to 65 years after the fact.