@idempotent1729,
I doubt that baronets can bypass descent in the right line by male descendants. I know of only one hereditary title for which an exception were ever made. The first Duke of Marlborough was John Chuchill (1650-1722). His son died long before he did, and by a special act of Parliament, his daughter Henrietta became the second Duchess of Marlborough upon her father's death. Her two sons died before she did, so the ducal line passed to the son of her sister Anne, who had married Charles Spencer, and so Charles Spencer the younger became the third Duke of Marlborough--the ducal line has been known as the Spencer-Churchills ever since. The father of John Churchill was Winston Churchill, and so the Churchill with which the modern world is familiar was Winston Spencer Churchill. His father was a younger son of the seventh Duke of Marlborough, so Winston and his son were out of the running.
You'll note that it took an act of Parliament to authorize that descent. I know of no other instance in which descent in the right line is set aside. The few examples of descent of a title through a female line of which i know are cases in which a daughter of a peer had an adult son living in the lifetime of the title holder, who could designate that grandson his heir--and usually that required the consent of the sovereign. Even that was not common--so, for example, during the Wars of the Roses, more than half of the peerages were extinguished in the direct male line--and no effort was made to pass on the titles, although they might be revived.
So i would say that the answer to your first question is no. The best biography of John Churchill (in my never humble opinion) is that of Winston Spencer Churchill, who had access to documents not available to other biographers at that time. For the Wars of the Roses there are literally hundreds of historically well-researched and reliable books.
The way estate law worked in England in the late 18th century, it might or might not have been a case that an estate would be left with no restrictions. Although i know of no source (which certainly not doesn't mean there isn't one), i suspect that most estates were entailed, or settled into trusts before the death of the testator. An entailed estate means an estate which can only be inherited if certain conditons are met. I believe i am correct in stating that entails are no longer allowed in England. They are not allowed in the United States to my knowledge. Entails usually were set up to assure the income of female descendants or relatives or wives, or to assure that an estate survived to support the descendants of the testator. Often, if a son were profligate, or the eldest survivor were a married female, the intent was to protect the estate from the profligate son, or the husband of the married daughter. Entails could be frivolous, too. Daniel Parke was born in Virginia about 1670, and he married into the Carter family, the richest family of planters in Virginia. He then decamped with all the liquid assets he could convert, and was not heard of again until 1704, when at the battle of Blenheim, the Duke of Marlborough called for a piece of paper on which to write a dispatech to Queen Anne to report his great victory. Parke pushed forward and presented the Duke his tavern bill from the night before, and the Duke wrote his dispatch on the back of the bill. He then gave Parke the dispatch to deliver, a great honor from which Parke, using his undoubted charm, managed to profit more than was usually the case by his flattery of Queen Anne. He was later made the Governor of the Leeward Islands, and was killed by a mob in Antigua.
His will left a legacy to a bastard son in London, and a bastard daughter in Antigua, and included an entail that required all of his descendants to take the name Parke. Although no one was certain the entail would stand up in court, it could taeke many years, even generations, to resolve such issues. So, Parke's daughter had married the son of a rich planter in Northhampton County, Virginia, whose estate was known as Arlington, after the estate of the rich planter's grandfather in England--that rich planter's name was Custis. His grandson took the name Daniel Parke Custis, just in case the entail stood.
His wife was Martha Dandridge. She delivered two stillborn children, and two live births. When her husband died, she met and married George Washington a few years later. Her children Pasty and Jack both had Parke as a middle name, and Jack's son was named George Washington Parke Custis. He had an estate near the Washington estate, which he named Arlington, in honor of his ancestors. Arlington is, of course, the site of the national cemetery near the city of Washington. I believe that the entail became meaningless after the revolution, when entails were eventually outlawed in all states.
Although entails were useful for securing estates against the profligacy of sons or grandsons, or the greed of sons-in-law, it was not the only method of securing an estate. A trust could be set up for daughters or grandchildren in the life time of the potential testaor, although for women or minor children, there had to be a trustee. In estates of the peerage, the Crown took a direct interest. There was long an institution of the royal government known as the Court of Wards and Liveries, which acted as trustee for estates of the peerage which had devolved upon women or minor children--and it made damned good money for the Crown, too, which usually looted those estates as much as was possible under the law. John Winthrop, the famous governor of the Massachusetts Bay Company, was a lawyer in the Court of Wards and Liveries before he got in the business of founding shining cities on the hill.
If you are asking this for the purposes of writing a work of fiction, i would advise learning as much as you can about the Court of Wards and Liveries, and about Chancery. Those were the two courts in which such matters would have been settled. I doubt if any estate of a baronet every ended up in the Court of Wards and Liveries. A baronet was not a very wealthy or powerful man. In fact, it was a money-making scheme of James I (think, King James Bible) in the early 17th century. He created the rank of baronet, and those whom he "honored" with the title were required to live up to a standard, which the King could conveniently assure by selling them an estate. If they refused to accept the title, they would have to pay a healthy fine to the King. If you've got sharp lawyers, being King can be a great racket.