You have just stumbled upon the reason why we always carry measurements out further than a single digit. Yes, a measured value of 100 is anywhere between 50 and 150. If you use several such measurements, then you arrive at a number between 2 and 6 in your last example. This is the reason why scientific notation was developed, and the ease of communicating one's degree of uncertainty is why it sees continued use, despite being less useful than engineering notation. (The difference between the two being that engineers only use powers of 10 that correspond to divisions of one thousand).
Propagation of error and uncertainty is a topic of great interest in the scientists, and there are a number of ways to communicate your degree of uncertainty to others. We typically use introductory chemistry courses as a platform for beating the notion of
significant figures into people's heads. Parts manufacturers can use another method, the one that springs most readily to mind is
resistor color codes. A first semester chemistry student would interpret red-purple-red-gold as 27x10^2, or 2700 ohms. Having two significant figures means the actual value is anywhere between 2650 and 2750. In reality, the gold band at the end means the error is 5%, so you're as low as 2565 and as high as 2835.
You may notice that I have not used repeating 9s at any point. Due to the way decimal notation works, 0.9 repeating is not a distinct number from 1. This can be shown with the fraction 1/9 and its conversion to decimal form. If I divide 1 by 9, I get 0.1 repeating. If I multiply 1/9 by 9, I get 1. If I multiply 0.1 repeating by 9, I must also get 1. Since 0.1 repeating * 9 yields 0.9 repeating, 0.9 repeating has the same relation to the number 1 as colour has to color. This exercise points out the shortcomings of our decimal number system.
Error and uncertainty is also introduced inherently by certain numbers. Take, for example, the number π, which people commonly know to be 3.14. It is actually more accurate to use 22/7 as opposed to the commonly memorized decimal. The fraction 355/113 is more accurate than 3.1416 (the "good" decimal approximation of pi) by over a full order of magnitude. Arithmetic operations on numbers are problematic as well. If I have to take the square root of a number like 2, I introduce error depending on where I round off the decimal. Much of the error accumulated in calculations can be eliminated by working with numbers in their exact forms, but since fractions and radical signs scare the **** out of algebra students, you're going to see fewer people working with exact forms the further left you go on
this scale.