To be good at any job requires time in and practice - there is no replacement for experience.
Here are some important things to remember when you're looking a job that involves caulking:
Temperature and cleanliness matter - check with the manufacturer specifications for ideal application temperatures and whether the material will react well with all surfaces.
Keep cleaning supplies handy - Some caulking materials may only require paper towel or rags to clean up. Others may require solvents like turpentine to fully remove any mess. Be aware of how the material is handled and how it should be cleaned up.
AIR sealing or WATER sealing? - Some materials are suitable for either air or water exposure, but may not be suitable for both. Be careful to use the appropriate caulking for the job.
Hire a PROFESSIONAL - If there's any doubt about your ability to do the job correctly, don't hesitate to bring in a professional. Renovators, insulators and air sealing contractors may be able to get the whole job done quickly, neatly and for a reasonable price.