I understand the larger a cone is, the worse it will be at playing back a higher frequency, but is there any guidelines on cone size one should generally look for when purchasing a speaker?
To keep things simple, let's limit this to 2-way speaker designs.
You've already got the general concept, that smaller woofers can go higher than larger woofers, as long as all other things are equal.
If you look at a woofer's Frequency vs. SPL curve, its break-up noise sometimes is visible as a prominent peak or peaks, but other times is not. TLS Guy provided some nice examples of these. In general, softer cone materials start falling off in performance or enter break up at lower frequencies that stiffer cone materials. A very rough order of soft to stiff cone materials is:
Polypropylene
Paper & coated paper
Paper doped with natural or manmade fibers, or wood pulp
Glass, Kevlar, etc. fiber
Aluminum
Coated aluminum (anodized)
Magnesium
Also, a woofer's Impedance vs. frequency curve can also show irregularities that occur at or near break up in an otherwise smooth curve. I'll try and find an example.
TLS Guy's examples also each show three FR curves. One is measured on-axis (0° off-axis) and the others are probably 30°, and 45° or 60° off-axis. A woofer's off-axis response deteriorates as the frequency increases, and this usually happens before woofer goes into break up. This feature is actually more important to designing a good crossover than avoiding break up frequencies.
Imaging is generally best when the drivers are radiating in the widest possible manner. As the wavelength produced by a driver approaches the diameter of the driver, the driver starts "beaming". It radiates sound in a smaller and smaller horizontal window in front of the speaker. Stated another way, imaging is the ability of the speakers, when operated in stereo, to accurately place the instruments and voices horizontally within the sound field. You need wide dispersion to achieve this.
(Before GrantedEV chimes in about wave guide speaker designs, I'll say that I'm talking about speakers with standard flat baffles, or 180° wave guides
.)
So the more important question is at what frequency does a woofer still produce widely dispersed sound. Look at the FR curves, on-axis, and at 30° off-axis. Pick a crossover frequency that is as high as possible, but where the frequency responses on- and off-axis are within 3-4 dB of each other.
For most woofers, this will be well below the frequency at which break up becomes a problem.