Before jumping in to this I would spend some time on budget research and figuring out what time frames look like. It may come down to something like 50k for a commercial mill to be done in 6 months vs. 20k to diy but it takes 3 years (just throwing numbers out to make a point, I didn't try and actually calculate anything). It may turn out there are no commercial sawyers nearby that will take the job, or only a handful of guys with portable mills that can cut it all up but the rest is on you.

A mill that can handle a 36" log is not cheap, and a piece of equipment that can maneuver a 36" log is also not cheap. You could probably get away with using a mid size tractor, but if you don't already own one its a major added expense. In my experience as a beginner, once you start hitting logs in the 24" range the difficulty level goes up. My mill has a 30" opening, I would call it a mid-level entry mill, and I don't like cutting anything over 24" if I can help it. I've never tried to set loblolly pitch, but I've seen it used as siding (unset) and it definitely will drip. I've seen solar kilns built relatively cheap, but building one you can heat for setting pitch is going to be more involved.

What is your end goal for the property (ex. build a house in the next 2 years), how many hours do you think you can put into this project per week/month, how soon do you want to be able to use this lumber, how much experience do you have running a mill? I work full time with 4 kids, I originally intended to run my mill one evening per week, which ended up being more like one evening every other month, so I have a huge stack of logs that turned into termite dust. Also I didn't really set up a good stacking/drying area, so my advice would be to set that up first.

I think it can but done, but I suspect it will take a lot longer than you might think. If you do commit then I would get all the auxiliary work stations set up first. Get the kiln built, get your stacking area leveled and covered, get your mill location leveled and covered, and get any moving equipment on site. I would start with one tree at a time if possible, just to get a good idea of the pace. I think the biggest challenge/decision will be what size mill to get. And remember all my advice is coming from an amateur hobbyist, so take it for what its worth lol, but there is a lot of good advice on this site. This project would be outside something I would take on, but I already own a mill too small to do the job and I don't have any plans to use or buy that much wood. Good luck and I'd be happy to answer anymore questions more specifically.