Hey Therrin, you feeling a little pressure? This is where principles and practice meet. I am sure Ekka has given you sound advice. Use your head, look at the situation from every angle, and act with conviction.
If the little voice in your head is still bugging you, it might be wise to find that mentor. You aren't feeling any more OR less pressure than other tree removal person has.
There seems to be room for a bit of error there (hard to tell from photos), but keep in mind to error on the side of caution. That means, its better to have to fix a driveway/mailbox/etc than it is to fix a house.
Use the knowledge you've acquired, and good luck!