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Your ladder question first…
It is difficult to handle a ladder of that length for most anyone. Putting it up and taking it down safely is a two-person job... not that one determined person couldn't do it but it takes a little skill and a little luck to get away with it. Two just makes it a lot easier and safer. Plus you can share the experience over a cool drink afterwards!
The difficulty with either raising or lowering a long ladder, even one that is not particularly heavy, is that the bottom does not want to stay on the ground once the top is raised, causing it to pivot in (or out of) the iron-like grip of the handler. Holding the bottom in place prevents an out-of-control ladder landing! Doing this alone requires the base of the ladder to either be somehow staked to the ground or to be pushed against an immovable object such as the foundation of the house, fence, tree trunk, etc. This provides enough stability so that the ladder can be safely lowered.
To put the ladder up, place the bottom of the ladder in position on the ground. One person stands with their feet holding the bottom of the ladder in place (their back towards the building) while the helper lifts the top of the ladder up, "walking" their hands down the rungs until the ladder is upright. Once vertical it should be fairly easy to handle (high winds excepted, of course) and put at the proper angle on the house. Most new ladders have a whole litany of safety info on them, including the recommended angle.
Getting a large ladder down (again easiest with two people) is accomplished by positioning everyone just as they were when the ladder was first raised. One person uses the feet to keep the ladder base in position while the other person "walks" the ladder, hand over hand, down to the ground.
Regarding your gutter guard question, my opinion is that if you are going to spend money on gutter guards, get ones that will need as close to zero maintenance as you can afford. Choosing the right guards depends on how easy it is for you to do "occasional" cleaning. Some types of gutter guards let virtually no debris through, but tend to be more expensive to purchase and install. Less expensive alternatives might work fine if your roof is low enough for sometime-maintenance. I suggest visiting GuttersDirect at http://www.guttersdirect.com. They have information on a variety of gutter cover products to help you to make an informed choice.
There are alternatives to gutters. Rain Handler at http://www.rainhandler.com, has a product that is a complete gutter replacement. Instead of collecting the water and directing it to a downspout, special fins catch roof runoff and disperse it into small droplets away from the foundation. The harder the rain, the wider the dispersion so the area next to the foundation never becomes soaked. Of course, this type of gutter is not for every home, since some landscaping problems or architectural features may require redirection of the water flow to prevent possible basement dampness or even leakage.
After years of looking at gutter guards, I have come to the conclusion that the only sensible type to purchase are rigid gutter covers… preferably galvanized steel or aluminum. The plastic-mesh type are too flimsy, tend to collapse under the weight of leaves and other tree debris and, even when working, let too much stuff through! Because of this leakage, the gutters have to be cleaned every few years anyway so there is really little economy or savings with the plastic covers… especially if you pay someone to install them!
Paying for regular gutter cleaning is an option too, but twice a year cleaning may not be enough! Since it only takes a small wad of leaves and one short stick to completely block a 30 foot long gutter, it can become expensive to continue to call someone for these little blockages. To help solve this dilemma, there are special metal downspout protectors that do a fairly good job of stopping this type of blockage, keeping a path for water to escape the gutter. They simply insert into the top of the downspout (from within the gutter) forming a protective, raised barrier allowing water a drainage path even when the gutter has some moderate debris in it.
ail or screw it shut so it doesn't blow open at an inconvenient time... like during one of your famous snow storms!