It does not always follow as one would maybe suspect that the more educated the person the better the handwriting. Although, it has been said that practice probably makes perfect, so when you consider the scratchy scribbles of ancestors writing their names, it is due often to lack of practice.
Writing changed over the centuries. Firstly, we had medieval and law scribes, followed by Elizabethan, then 18th century, on to Victorian and modern day. Latin played a big part pre-1733 for legal documents; it was officially dropped after that but does pop up.
In reading old wills the technique is to slowly accustomise yourself to the first eight to twelve lines or so. These documents tend to start with the same standard text and phrases. First giving the name, the abode, the occupation; then moving on to the state of mind or health of the person; and then a religious statement and funeral wishes. So, for instance, the will may well begin as follows:
"In the name of God amen. I Richard Spear, farmer of Colmworth in the County of Bedfordshire do hereby make this my last will and testament. Being of sound mind but weak of body_____." and so on_____.
Using these first lines, it not only gets you used to the scibes form of writing, but the likelihood is it will cover most letters of the alphabet for you to follow on and use to transcribe the document. So its worthwhile to linger on these stock phrases, and then work on the rest of the will.
Abbreviations are often used, especially names:
John will be Jno Jo, Joh, Jonas
James will be Jas, earlier form as Jacobus.
William, often Will, Willm, Wm, sometime as a W with a squiggle above. And earlier Guillem.
Joseph as Jos
Robert as Robt
Richard as Rich.
Other abbreviations can cause problems and are sometimes singular letters. The word which, for example, can be seen as a capital "W" with a small "ch" above it. For the word with, that can be written as a capital "W" with a small "th" above. For the word "That", it can be written as a letter Y with a small t above, now that's confusing !!! For "this" it can be a letter "Y" with a small "s" above.
With wills there are sometimes wiggly lines at the end of each line, and these can be confused as being letters or words. This is so that when the will is finished nothing else can be added. Money is sometimes written in latin:
Pounds = librae
Shillings = soldi
Pennies = deman
The national archives in Kew, England has an online tutorial which you can follow through with lessons of varying difficulty; they are free and worthwhile, if you want to improve your skills: http://www.nationalarchives.gov.uk/palaeography/.