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There are plenty of machines to choose from, so be choosy. Most that you will find are homeowner used machines. Some aren't - ask the seller if they were used commercially. Also ask any seller how much lawn were they cutting on their property. Anything over an acre means it has been used quite a bit. One thing you will find is that the lower end tractors & riding mowers (Craftsman LT1000's, and any Murrays or MTD's) are usually about near the end of their usable lifespan when they are offered up for sale UNLESS they were meticulously maintained. Always ask the seller if the blades wobble when grasped & wiggled from under the cutting deck - if they do wobble, the spindle is worn out or has bad bearings. This can easilly be a $100+ repair, even if you do the work yourself. Spindle replacement will cost at least $200+ at a shop, and you have to get the machine to the shop & back home (most shops charge about $50 for pickup & delivery). Heres a quick rundown of other things to ask in addition to above:
Does the engine smoke or make any strange noises? Does it run smoothly at ALL speeds? Does it start promptly cold or hot?
What condition are ALL the belts (cutting & drive belts)? Belts can run $30 each, plus installation if you're not able to replace it yourself!
Condition of tires? Do they hold air?
Any steering "slop", excessive turning of the steering wheel to make a slight turn?
Is the deck rotted or banged up? Means it was possibly subjected to rough terrain & neglect...
Do the safety switches work? These protect you from SERIOUS injury!
Is the owners manual included? If not, try to see if you can obtain one before purchase. VERY IMPORTANT! It covers operation, safety, and parts numbers for when (and if) you have to perform repairs.
Where was the machine stored? If outside, its probably a rust bucket - pass on it unless it REALLY is rust free, clean & otherwise decent. Also, being kept under a tarp while outside traps moisture - not a good thing either.
An original owner should be able to tell you the exact age of the machine - if not, be a little suspicious. If they say "five to seven years old", its probably older than what they tell you, OR they are NOT the original owner. Find another machine because who know what else may "escape" their memory!
Ask lots of questions. A bad seller will dodge answers or ignore you - do the same if this occurs & find another machine. I can give you my HONEST OPINION of a machine, even if its a local competitor's mower. If its good, I'll tell you so. If its crap, I'll also tell you so.