@Cooter I understand and appreciate the insight.
We've got an Allis Chalmers D19 with a front end loader that has spikes on it. It hauls trees of the size we're dealing with pretty well. Generally need to cut the thing in half and then drag it across the ground if they're more than around 20-25' tall, which some of these are but most aren't. Leaves a bit of a mark on the ground, but nothing too bad. The tahrs on the D19 are a lot easier on the ground than a dozer. We've got other tractors (Massey Ferguson 165 and Farmall H) that can drag some of the smaller bits around, but really the D19 is the best of the bunch for any moving/dragging.
Chainsaw, the #1 we have is a 20" bar Jonsered (rebadged Husqvarna for TSC) that does a good job and makes quick work overall. Got an old 14" Poulan as well (my wife had that when we got married) that we never use, but works fine for small items. Actually the Poulan hasn't wanted to start for a while, need to look into why that is I suppose.
We have a bonfire each year in April, and have a designated bonfire area on our property for the burn wood. So basically we expect grass to never grow there again. As soon as one year's bonfire is over, we start putting more wood on the pile for next year. We've got a few corners of the property where we can easily keep wood that we'll use for the next year where it's out of the way of anything we see or do, and out of the way of where the runway will be.
Also definitely agree on safety - that's top priority and it's real easy to die fast if you're careless working around this stuff. We're inviting some friends out to help, but not going to just hand someone a chainsaw and say "Go chop down that 50' tall, 24" diameter tree over there that's right next to the house." Mostly the social aspect will be for fun and to have some extra hands with some of the easier bits that need cleared.
The other aspect is making sure we remove the exact trees we want. We have a pretty good idea but reality is that once we get the basic runway layout cleared we won't know. We'll probably chop down some additional trees to give more width. So from that perspective, chopping the trees down first makes sense and then if we're going to pay a dozer, we'll be able to basically pay it for the job of pulling the stumps and doing any ground leveling all at once.
Correct. Knowing which way the tree will want to fall is important for simple tree felling. Sometimes you have more complex situations where it needs to fall the opposite direction of where it wants to. That gets harder.