Im working with a small funneling treeline running from larger woods to a smaller set of woods. The land i have access too is in side the black box. I was trying to gather other opinions on hunting this funneling treeline (1) since the larger woods(10+acres) are all to the north. Or should i just hunt inside of the woods (2) on the small section of land I'm allotted

Have you scouted it out, yet? Need to look for sign and maybe do some glassing early in the morning and late in the evening.

I would have stands in a few spots. Let actual ground conditions and wind direction tell you where to hunt any given day. You have lots of options there.

what John said.

I will add, The prevailing wind early season will be S or SW. Face into it or quartering and only hunt with a favorable wind. Be down wind of where you expect the deer to travel based on your ground scouting.

The other thing to consider is how you will enter and exit without spooking deer. Find where they bed would be key if you can...the best time to do this is in the winter when the season ends so you need to "tread lightly" this time of year with your scouting.

What I want to know what you are doing up at 4.44 AM ? It,s dark , most people are asleep , or going to work or bathroom .
As arlowe13 said . Do your homework LOL

I have similar set ups on my property. Small woodlots and a heavy fence lines. You need to scout everyday every hour. set up trail cams and get a general idea of how they are useing the lay of the land. deer are pretty predictable once you figure out there routine. Invest in a good comfortable climber stand and just start hunting. pay close attention to wind direction. I have some stands set up such that i can see well over 500 yds in either direction. Invest in a good set of binoculars ( 10 x 42 ) and start putting in seat time.

Istay out of the woods , catch the deer going to bed I have hunted small plots like that seem you will find tracks are all in the same direction if going in a morning hunt planned coming out evening hunt the woods will be the bedroom So stay out imo

Definitely through my experience with these guys, is I would scout it and glass it. If possible try and put a trail camera(s) in both spots and see where most activity is coming from and find out the deer's daily routes and which wind direction there moving in and then go from there. You still have a lot of season left so I would suggest you figure that out and then go in there a slay one!

Just I say don't be going in there too much because you could easily push the deer out of there.

In my experience, always hunt 30-50 meters from a corner. Never on the corner. Just my 2 cents

Well one shot let us know how or what you decided