Slyder,
First let me say that these guys are absolutely right - IT'S NOT WORTH GETTING HURT!!!! The way I see it, your biggest problem is not having enough experience and knowledge to recognize the hazards that are right in front of you. If you're a smart guy, you can probably figure out how to solve the problems and get the trees down, but overlooking a problem or danger could flat out kill you. Seriously, you could easily make a mistake that would leave you dead. Think hard about that before deciding to do it yourself. Nobody can judge you well enough over an internet forum to know if you’re capable of doing this or not.
That said, I was in your situation a few years ago. I got the quotes, figured I could find better things to spend the money on, liked the challenge of doing it myself, more tools / toys are always welcome, etc. I think I did just fine, and I continue to do tree work including climbing for family and friends.
It's a tough call by looking at those pictures, but I think you may have options if you decide you want to do it yourself. You're a remodeling contractor, right? Well, I'd say that doesn't look like a $2200 shed, so maybe if you do it yourself and wind up damaging the shed that's not such a big deal. You can fix it yourself and probably for much less than $2200. I don't mean to say that damaging the shed is a legitimate option, just making a point that a DIY'er has a different perspective from a professional tree guy. Now for a reasonable option - can you move the shed? It looks relatively small and appears to be on blocks. Maybe screw a couple 4x4's under it to use as skids, and pull it 15' towards the road. If you can move the shed, the dog cage, and the gas tank, then would it be possible to fell the whole tree parallel to the road or maybe what I'm guessing would be across the dirt driveway and into the side yard? There are a lot of different ways to look at it if your main goal is to get the trees down, learn something new, and have a little fun doing it. (Some folks on this site don't like it when "hacks" like me call fun an objective of tree work, but hey – it’s fun to me.) What are you going to do with the wood? That’s a lot of wood for the average person to dispose of, but maybe you’re going to burn it or have a connection to get rid of it. (Bobcat, dump truck and a place to dump it?) Are the power lines on your side of the road, or the other side of the road? Is that a busier road than it looks, or a rarely traveled road? Warning / stopping drivers should be an absolute must if there’s any chance of something winding up in the road. Safety of everyone around from yourself to people who might wander by should be your biggest concern when trying to figure out how to do something like this yourself. Hire somebody to do it, and it’s all their problem.
If you’re not too far away from northeastern CT, I might be willing to help. If you want to post more pics, I’m sure I’m not the only one who would be willing to keep trying to come up with ideas. Actually, you seem to be getting a friendlier and more constructive response than I’m used to seeing on this site. Maybe somebody will come up with a solution that’s reasonable & safe for you. Could you move the shed and drop them next to the house? How ‘bout a pic from far to better show the height of the trees compared to the house? I’m wondering if your pics are deceiving and making the trees look taller than they are. Pics of potential drop zones? Even if it has to be climbed, moving the shed, dog cage, and gas tank would eliminate the need to do any rigging.
Sorry for the long post, I guess I just wish there was a better way for guys like you and me to find help getting started. Looking back, I consider myself lucky to have survived my self learning process thus far. I may be way out of line here, but I’d guess that some of these professionals feel similarly about the way they learned, and that’s why they’re so tough about giving advice to people who want to do it themselves.
Don
