Suggestions on first equipment to buy?

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I tend to do small to medium sized trees, no more than 60' in height and no wider than 36" at the base.
I currently have my personal Tundra... Which is the reason I was leaning towards an F-350 dump truck.
I have been finding the F-250 / F-350 dump trucks in decent condition for around $6500 and chippers in decent running condition for around the same.
The only problem with the mini skid steers is they tend to cost around $20k for used. I just got quoted on a new Bobcat MT-100 with the grapple at $38k, but there is a 4 month waiting list.....

I just want to make sure that I spend my money wisely and get the most production value out of the $15k I have to spend. I hate dragging branches, but I also hate loading big rounds by hand. So not sure if going the route of a chipper or skid steer is the best option.
That's a good price for a solid dump/chipper. I'd jump on that with the intentions of going to a larger chip truck down the rd. One of the considerations is that you will need to make multiple trips to the site unless you have another driver. This seems to me the point where guys decide to go for it and get employees, or to work for others.

I use my tractors on many jobs, but they don't have the lifting capacity a skid has, or even many mini's have. That being said they are also lower impact than an 8-12k skid, and they do a lot of work for me, so I'm multiplying my strength. I do a good bit of dirt work too, so I'm not specializing in tree work. I have a skidding winch on my larger tractor that allows me to take on jobs that others would have to rig out without climbing/rigging, so I can do them by myself and charge a little less than others with a crew/more equipment/overhead. Then when I have a stump ground I remove all the chips with my little tractor and I bring in around a 1/2 yard of topsoil to avoid the sinkhole many get after a large stump removal. Many tree guys here do not do the dirt work, grind the stumps and then leave. While I'm limited on what jobs I can take, I offer the dirt work and stick around the job site a bit longer, which obviously makes more money.
 
So, from the replies, it seems that a skidder would give me more productivity than a chipper....
I just hate dragging limbs, and then they take up a lot of space forcing me to take more trips to and from the job site.
 
My vote is for chipper and dump.
I’ve spent too many hours mulching up piles of brush with a saw in the back of a truck. It’s miserable, it’s hazardous, and at least around here it’s harder to get rid of the material afterwards.

A mini skid is a productivity game changer for sure, and noodling big rounds to be able to handle them sucks, but I think you’d still finish most jobs faster with a chipper than with a mini. Not all jobs, but most I’d wager.
 
So, from the replies, it seems that a skidder would give me more productivity than a chipper....
I just hate dragging limbs, and then they take up a lot of space forcing me to take more trips to and from the job site.
I think a chipper and a dump truck at the prices you say you can get them sounds best. Then buy an arborist trolley to haul limbs to the chipper.
The skidding winch is a tool I acquired to pull tops to the trail for making firewood to sell while keeping my tractor out of the woods where it would get beat up(even more than it is). It does have its uses, but they are limited, since I already have it I incorporate it into the work I do. I rarely use it to drag brush as it would tear up the yards, I primarily use it to pull trees against their lean or to swing them 90 degrees off their lean, but I have used it a few times to pull brush when the ground was thawing and I couldn't drive to the brush with my tractor because it was too soft. I will also use it as a GRCS on trees that allow for it, I can tip tie a rope and then pull branches up, and once they break the hinge I can drop them back down but first. I also will tie off a whole tree and notch it towards another tree I have a pulley in, then give it a pull just as you would with a GRCS, and cut it from the bottom up just as you do with a tip tied branch.
 
It all depends on location, dump sites, number of employees you're working, etc. If you've got a place to dump debris for free or cheap close to your work area, you can start out with a dump trailer and the machine you decide on, whether skid steer, tractor w/grapple or whatever. I can't imagine working without a loader of some sort, you will work yourself to death without it on a job of any size. As you already know, if you cut small before you load it you can pack an amazing amount of limbs and brush in a trailer. If you don't have a dump site, the chipper will be your best option but the more equipment you have, the more vehicles and men you must have to move it around. Getting rid of chips is normally not a problem. If you go for the dump truck/skid steer option, remember that loading over the side of most dump trucks is a stretch for small loaders.
 
rjstamey, I'm in the exact same boat buddy!

I very recently went from leading large forestry and tree service crews (company sold) to starting my own business and trying to work for myself. I'm unfortunely accustomed to using all the nice stuff...skid steers, chippers, dump trucks, cranes, excavators, etc. I'm currently doing the same types of jobs with my 1/2 ton Sierra and a high-sided 14' trailer...it sucks!

If I were you I would focus on acquiring a decent heavy duty dump bed truck, and build out a chip box on it. There are plenty of smaller chippers with low hours for sale on the forestry-tree trader pages. You don't need to chip up 14" diameter trees, so something that chips to 6" or so would be great for a few years, firewood the rest of the wood. I routinely burn slash on my forested properties, but trying to get away from that as insurance rates are thru the roof and the fire risk/liability is just too great in my area. I can rent or subcontract a guy with a tracked Bandit to come out and chip in the woods if need be.

Yes dragging brush to the chipper is a pain and it's a lot of work. But take it easy on yourself and your body, take your time and just pass the cost onto your clients. I have a Kubota I bring to some jobs to skid brush with, but if the jobs going to be a humongous pain the butt, just pass on it or bid it high.

Good luck amigo, let us know how you fare!
 
if the jobs going to be a humongous pain the butt, just pass on it or bid it high
Being limited as far as equipment and help, this is what I do. I also let those I'm quoting the work for know that they should inquire with others for bids as the costs will be higher because I need to rent equipment or it will take multiple trips. What's nice is that when I get done telling them this, they often say "when can you start". There's a reason I'm there giving a quote, many times it's about trust as long as the price is what they would deem reasonable. Most of my clients are willing to work with my limitations because I come highly recommended :).
 
Most of my clients are willing to work with my limitations because I come highly recommended :).
And that says a lot in the chainsaw/arborist business, if they know you are good you not only get repeat business but they tell their friends...
 
I started with a Chevy 2500 and landscape trailer.
Same as you as a side hustle
Then I bought a used 16’ dump trailer saved so much time offloading
Next I bought a skid steer at auction s650 23000
Bandit 90XP chipper
Traded that skid in for a t770 with high flow old skid+ 18000
Then dump truck ram5500
Then stump grinder attachment 7300 auction also
Tilt deck trailer next don’t remember that price off the top of my head (first brand new piece)
And just bought a 72’ track lift

Everything is paid off all in the last 4 years but I do work in northern VA
And I manage a large cattle farm so I am able to rent some of the equipment to the farm and help pay for it that way
Still only as a side hustle but I would love to find a good full time employee
 

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