Firstly, it pays never to make assumptions about these vehicles.  You need to check it over and then have it checked by a reputable mechanic.
That said, I would say that $25,000 for a 1999 with 190 odd K is slightly high, unless you would definitely spend the money on the accessories.
Defenders (and probably Land Rovers in general) require a little more owner awareness than the average modern sedan.  A Defender is a utilitarian vehicle not a 4wd lounge chair, and while comfortable enough has levels of NVH that many would consider unacceptable, and has idiosyncrasies that include leaking footwells and water coming in over the doors.
When you say "family of four" I take it that is the total - not the number of children?  Kids LOVE Defenders - the rear seating is elevated and the view forward and sideways is great for them.  But getting four of them in is a problem. The "third row", if fitted, faces inwards and is not the most comfortable.
Rear storage is fabulous, especially with a cargo barrier. After all, its a space capable of seating four adults.
People, even sane people, take Defenders everywhere.  Unless you plan on going VERY far off the beaten track a stock Extreme Defender (which has traction control and ABS) will get you there and back without trouble.
				
			 
			
		 
			
				
			
			
				Steve
2003 Discovery 2a
In better care:
1992 Defender
1963 Series IIa Ambulance
1977 Series III Ex-Army
1988 County V8
1981 V8 Series 3 "Stage 1"
REMLR No. 215
			
			
		 
	
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