RE: Hunting alone vs with others...
Good luck John
Dont be afraid to get out there and do it on your own. If you understand and adhere to the safety rules and area laws just go ahead and do it.
As far as field dressing a deer, it's actually pretty simple. There have been several videos posted here on how to do it. There are also many publications that show how. Take your time with it. Some tend to want to rush it and wind up puncturing things they didn't want to including themselves.
My first hunt, 4 years ago was with my 12 year old daughter. Neither of us had ever gone before. Like you, i asked lots of questions of the people on this site and learned tons. She killed a deer that day (youth day). Best hunting day of my life.
Just get out there and do it John. I'm sure if you have any questions before you go the great folks on here will help you.