The three conditions vary from eclipse to eclipse and from person to person. Thus I will expand on them.
Eclipse Totality Path
Getting in to the eclipse totality path is a matter of planning ahead. Some eclipses can be very difficult to reach because you have to go to the North or South Pole. Some are easier like just down the road a bit. How do you know? By exploring eclipse maps for upcoming total solar eclipses. The path of totality is a narrow band about 100 miles thick that stretches across the planet. Many times this band crosses oceans and just a little land (the Earth surface is 3/4 water). Sometimes large swathes of a continent are crossed as is coming in 2017 for North America. The eclipse path stretches from Oregon to South Carolina.
The following web pages provide maps of totality paths.
For great maps of the 2017 Total Solar Eclipse
Under Clear SkyThis is the hardest of the three conditions. The weather changes from day to day and sometimes multiple times in the course of a day for many locations. Finding a clear sky is never a guarantee of any eclipse expedition. Local weather information is often the best source for day to day changing conditions.
When planning an eclipse expedition the general idea is to look at climate. Climate studies highlight the weather of the past and can be used to guess at the future weather. Of course, it is a guess. When traveling great distances the climate study is very important but when journeying a short distance it may not be as important. More important is the ability to relocate quickly should the conditions arise.
My own best solution is to have a contingency plan in place. Checking local weather information in the days prior and then moving to where the sky will be clear makes it much easier to reach clear sky.
Here is a great link for weather/climate information as it pertains to Total Solar Eclipses:
Where you are comfortableA big variable based on the person. Some are comfortable being in nature, exposed to the elements, with only the supplies you carry. Some are more comfortable near a toilet and shelter from the hot sun or freezing wind. It depends greatly on the location and weather conditions at that time. In addition the presence or absence of people can make a difference in terms of comfort. I can tell you from experience it is very uncomfortable to set up a telescope and camera near a group of playful or dancing youth. That's just me though.
I like being in an open area with facilities and shade near. The parking lot of a hotel, an open meadow in a state park, or even a roadside rest stop make for a fine location. I am not as interested in the scenery as the eclipse so it does not have to be in an epic location. And really - seeing a total solar eclipse take place in a somewhat normal setting adds greatly to the surreal aspect of the experience.
Groups are not for everyone. Some prefer solitude or a small select gathering of just friends. I've heard some great stories from eclipse chasers who went this route. Most involve encounters with wild animals, maybe another blog entry at a later time....