A good-quality 100' 12 gauge extension cord is a good choice if you really only want to have one cord. The plusses outweigh the minuses.
Rarely would anyone need a cord bigger than 12 gauge, and only with very large amp-draw tools would there be a worry about the voltage drop and increased resistance (heat!) that comes with the extra length. Tools like a 9" angle grinder a BIG breaker hammer like a Bosch Brute or an electric compressor really should not be used with more than 25' of total cord as the armatures will burn up before long when the tool is put to the kind of work it was intended to do. Portable compressors do better with less power cord and more hose to cover distance. Shop air shouldn't get an extension cord; plug directly into wall only.
Household extension cords max at 15 amps because standard 110V residential outlets are 15 amps, I think it's CYA stuff. Smaller gauge cords will be rated lower but a cord over 15 amps is specialty or commercial use and rare anyway because that much power going through a cord isn't a good idea at almost any added length. A 12 gauge cord technically should be able to take 20 amps and 10 gauge should do 30 amps, but often the makers just rate them for 15 amps. Really big electric-powered tools typically have the max cord length at the right gauge fixed to the tool at the factory and warn to never use an extension cord.
If a large amp-draw tool (as opposed to very large, meaning not as big as the ones mentioned above) is pushed too hard and bogged down during a particular use, the 100' cord will help fry the tool before a shorter cord would, but bogging down an electric tool is the quickest way to kill a tool anyway. An abused tool won't last, it will just go more quickly with a longer cord. Toasted armatures are almost always too costly to repair to be worth it and service centers can generally tell if the tool was pushed too hard by looking at the armature. If there are no shorts elsewhere in the tool or any bad bearings, nearly every premature failure of an armature is due to improper use which means a denied warranty claim.
If it is not possible to get within 100' of a power source, the source needs to move or change, like to a generator or the outlet on the back of your
neighbor's garage.

Using more than 100' of cord is just asking for trouble.
For general use like you suggest and if you don't have any big amp tools to deal with, get the 100' now and get a 25' cord later only when the need comes up. Having one of each of those sizes in 12 gauge covers just about any need a homeowner would have, save Clark Griswold-style holiday light displays.