Some gutter work is genuinely within reach of a careful owner: clearing downspouts, re-securing a hanger, resealing an accessible joint. Sizing, pitch, seamless runs, fascia repair and anything at real height are not, and the reason is usually the ladder rather than the gutter.
Gutter Answers connects you with licensed local companies. We are not a contractor and do not perform the work ourselves.

The dividing line is not difficulty so much as consequence. These jobs fail harmlessly if you get them slightly wrong, and they do not require you to be anywhere dangerous.
These fail expensively, invisibly, or dangerously. In most cases the cost of getting them wrong exceeds what you saved.
The risk in gutter work is the ladder, and it is not a small one. Falls from height are the serious injury in this trade, and they happen most often on short jobs where someone did not set the ladder up properly because it was only going to take a minute.
If you do go up, the basics matter: a ladder on firm level ground, secured at the top where possible, someone else in the house who knows you are up there, and no leaning sideways to reach the next section. Move the ladder instead.
Three things that are hard to supply yourself: the height access and the insurance that goes with it, the equipment to form seamless runs, and the judgement to spot that the fascia behind the gutter has gone before it becomes a bigger job.
A reasonable middle path is common. Handle the routine clearing yourself if you can do it safely from the ground or a low ladder, and bring a company in for anything structural, anything high, and anything you would be guessing at.
Not always. Clearing debris and resealing one reachable joint are reasonable jobs. It becomes a false economy when pitch, sizing or fascia are involved, because getting those wrong costs more than the work you avoided paying for.
Sectional gutter on a low outbuilding is a realistic project. Seamless gutter on a house is not, because the run is formed on site by a machine that comes with the company installing it.
Work from a ladder on firm level ground, secured at the top where you can, and move it rather than leaning out to reach further. Tell someone you are up there. If the run is above single story height, get someone in.
For clearing and simple sealing, no. A stable ladder, gloves, a scoop and a suitable sealant cover most of it. Forming gutter, setting pitch accurately and fascia carpentry all need equipment most households do not have.
When the job involves height you are not comfortable with, when you find soft board behind the gutter, or when the same problem returns after you fixed it. The last one usually means the cause is not where you were looking.
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Tell us what your gutters are doing and we will connect you with licensed companies working in your area. There is no obligation to hire anyone.