There are two things that you would need to keep in mind while you are in the air.

First is the route back to your landing strip - where are the highest trees, what is my glide like, can I get back?

Second is the fact that if there is any breeze at all, then it will likely cause very noticeable turbulence - horizontal rotors - across the field. As these bleed off the downwind side of the field they might also affect your decision making in the first question.

You have not given any indication of the size of the field you are thinking of using. I have based my comment on a square - say 100 yards each side - which is about as small as I would think you could operate a histart from.

Mind you, on a good day the upwind edge of the field could be a goldmine of thermals!![8D][8D]