Pretty tough question without seeing what part you want to draw up. But generally, you look around for the most important surface on the part, whether it be a hole or a planar surface. The most important surface will be a machined feature, not a cast or molded feature. Sometimes, the most important feature has a phantom location, meaning you must deduce where the geometric center is relative to a mating part. Then you take measurements from the most important surface and begin the process of deducing where the other features of the part are located.
A bit of familiarity with common fasteners, bearings and seals would be a big help. Obtain catalogues from bearing and seal suppliers. This can help you figure out the exact diameter of important bores, rather than slavishly copying what might be an out of tolerance or worn out hole in the sample part.
Hole patterns can be complex to figure out (sometimes). Think of an engine bell housing as an example. You'd need a caliper to measure the distances between holes accurately. Pick any two holes to serve as a baseline.
Pick one hole and take measurements to various the other holes on either side of each hole. Deduce the center distance (because hole diameters may vary). You need as many hole distance combinations as you can make.
Then plot the measured distances in CAD as a series of circles, using the intersections to determine the location of the unknown holes. For example, from your baseline hole pair (the datum holes), you would take a measurement from each datum hole to the next hole. Plot those measurements as circles, and the intersection will locate the first unknown hole center. Obviously, the more combinations of measurements you make, the more circles you can plot, and the more sure you can be of the actual hole location.
Some sort of a flat plate (a surface plate) and a height gauge is also a good way to reverse engineer some stuff. But you'd need to spend a bit of money to get there
First you get good, then you get fast. Then grouchiness sets in.
(Note: The opinions expressed in this post are my own and are not necessarily those of CNCzone and its management)