Danielle,
Make sure the fonts are installed on every machines involved. So if Design and Watch are on two separate machines, you need to install the font on both machines. Another good idea would be to make sure you check the option to embed the fonts in the PlanetPress Image Output properties(under the PDF tab, check "Embed all" in the Font options).
Note that not all fonts can be freely embedded in a pdf. Sometimes, there are restrictions on fonts regarding embedding. You'd need to contact your font's provider to know if you can get an embeddable version of the font.
In any cases, if this is an urgent matter, please open a technical support issue. We will be able to investigate the behavior of PlanetPress for problem 1, and confirm whether or not we can embed the font, and if so, we'll help you make sure it works. You can go to our web page, and then Services->Support->Report an Issue. Or, you can call 1-866-348-5863.
Regards,
Rapha