I think the experience of myself and my partner may be instructive.
Neither one of us had owned a plane before, but we wanted to be owners and give it a try.
We shopped around and found Juliet. We did our research and found the airplane to have a history as a solid little airplane, generally well cared for, but with an engine well past mid-time and pretty spartan avionics.
Given the engine and the avionics, we were able to purchase her for a reasonable price (and an owner that HAD to sell). We have had a positive ball flying this little bird, but it has served to underscore some of the things we want.
So we are looking at upgrading. The decision has not been positively made, but, to be satisfied, there are some things we need to do to Juliet if we plan to keep her in the long haul. The existing radio works OK, and is serviceable, but isn't a true flip-flop, and is shorter range than higher end radios.
Also, if we decide to keep the bird, we will be looking at an engine overhaul in the next couple of years.
This whole approach has worked out pretty well for us so far. We will see how it works out as we go along. The main point, is that we bought a solid airplane, nothing fancy, for which we did not pay too much, as an introduction to aircraft ownership.
The "solid" aircraft part was a careful balancing act. Juliet is a pretty little bird (see N8346J in the photo section), flies nicely, and has been well cared for. So there have been no major mechanical issues.
So, now, we are looking at options. There is still time left on Juliet's engine, which runs sweetly, uses very little oil, has good compression and sips gasoline. So we can probably sell her for what we paid or maybe even a little more.
We like many things about the 150, so we might buy another 150. Or we might do the upgrades to Juliet.
The other factor is that the ONE thing about 150's that we really are not happy about is useful load. I tip the scale at 205 (yes I can get down to a lower weight, but I get grumpy trying to stay there), Vince is a lot more scrawny, but he has four kids (well, three and one on the way) and would like to take along more than one at a time. So that may weigh into the decision.
Soooo, buy high or low? Depends on what you want to do. We bought fairly low, but the low price was not based on "fixer upper" issues. It has worked well for our purposes.
If we decide to sell Juliet, the next purchase will be a "buy high" because it will be an airplane we intend to keep for an extended period of time.
And, yes, if we decide to sell Juliet, this forum will be the first to know.
Reg