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If you see a motorcycle just as a means to get from A to B, then a 250 is good enough. It is a basic level of transport with excellent fuel economy. It can keep up with traffic, and in those cases where traffic is going faster then it, the traffic is light enough to get around the 250 (if there is NOT enough room, everyone should be going below the max speed of the 250 anyway, do to other vehicle and shear volume of traffic).
On the other hand if you want a cycle to be a motorcyclist, then a 250 is to small. You want the bigger bike, even if you never go anywhere near its max speed. You will justify the extra power for various reasons, such as keeping up with traffic, being able to "Speed out" of an accident, etc. If that is how you view yourself a 250 will become to small in a hurry.
In between these two extremes are people who can justify the bigger bike, but they tend to be people like police who want to chase down fast cars, people who want to go form coast to coast on a bike (and thus want the extra power) etc. A lot of people think they are in this group when they really are in the second ground above, but how you view yourself is important so do not underplay it to much.
Comment of self-image. Marketers have been playing on self-image for years, successfully getting people to buy things they really do not need. You have to be careful of this in yourself, remember bike makers spend millions if not billions of Dollars to get you to buy their bike, and bigger bikes are more profitable then smaller bikes (and thus the push to get people to buy bigger bikes).
The classic tale on this subject is a story I heard in my marketing class in Collage. The auto companies involved were omitted from the stories (For the reason that the companies did NOT really want the story tied in with them, for it show how careful the companies are when it comes to marketing). The story went this way, two auto companies did a survey on the American people. The first company ask people want they wanted in a car and people told them they wanted a sensible, economical car that had good interior room, good fuel economy and just enough engine to go to and from work and a safe car. The other auto company asked the same question BUT not what the person being asked wanted, but what did his NEIGHBOR wanted in a car. The response was big car, lots of chrome, big fins (This was from the 1950s) and to hell with safely and fuel economy. Each company built its cars based on the result of their polling. The first company, which made a small, safe, reliable economy car went out of business, while the other company, which built large cars with lots of Chrome and huge fins made lots of money (I suspect the first car company was Kaiser, which tried to break into the car business in the 1950s and went out of business for its cars were not popular while the later was Plymouth whose models in the late 1950s had the biggest fins, most chrome and worse fuel economy and safety record. Kaiser went out of business while Plymouth prospered till the 1990s).
I mention this for the simple reason the motorcycle companies have spent almost as much money as car companies when it comes to convincing you what you need. They also studied people and cater to their weaknesses (and you are in the "Marketing" segment most converted by any seller of goods, you are a young male. Your buying habits are NOT yet fixed, that begins with your first bike (and car). People tend to stay with a brand their entire life, a brand their often unconsciously start to use in their teens and early 20s. Once "hooked" the company selling that item can count on you buying replacements of that item from that same company (People do change even in the dotage, but as you age you change less and less, that is just how people are, we are creatures of habit and thus will repeat what we did previously unless we have very good reasons to change).
I bring this up for many people view cycles as just a means of transportation (as is walking), but the majority of people put their self-image of themselves in HOW their get around. You have people who want to appear to be successful so their buy Cadillac, even through for all practical purposes the ride of a Caddy (Since at least the 1960s, prior to the 1960s Cadillac were built with better suspensions then Chevrolet's but all that tended to end in the 1960s when the cost of building better cars became just a small part of the actual cost of building a car) is the same as a Chevrolet. The difference between a Cadillac and a Chevrolet over the last 40 or so years is rarely a difference in ride or engine but image and extras on the cars (And most of the Extras you could get standard on a Cadillac were available as options in Chevrolets starting in the 1960s).
My point is simple, make sure you are getting what you need, NOT something you have been told you need by marketers. I rode a 250 in the 1970s and except for interstate highways was fast enough(and on interstates other cars could get around me as I rode on my 250 EXCEPT where traffic was to heavy and then most of the cars had to slow down to my speed even as their barely passed me).
Side note: Over the last four years I have been driving a 80cc motor scooter. It gets up to 40 mph on interstates. On the interstates I do travel on, almost all are inner city so traffic is already going around 40 mph just do to the traffic volume. I also take it on a four lane NON-limited access highway (which is being converted from a two lane highway). On the two lane parts people get upset that I can not go over 45 mph, but on the four lane sections they just pass me by and leave me alone. A 80 cc is to small for most highway use but I mention it to show you that speed is NOT necessary, and is only really needed on roads where faster traffic can NOT get around you. Such roads are also to be used by Pedestrians, bicyclist and horse drawn wagons so such high speed driver should be going no faster then 55 mph on such roads and a 250 can clearly get up to that speed, I have had my 80cc get up to 50 mph (yes it was downhill but it did hit 50 mph). When I had a 250 it was more then powerful enough to stay at 50 mph even up hills and unless you are on a high speed, low volume highway a 250 is more then enough engine.
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