Well....I think it will, provided it has been used regularly. If you find one in mint condition with low miles I would say that is the worst one you could buy. Anything that has sat for years on end will have a huge build up of items that need to be taken care of. When we were looking it was very common to find one that had sat for 3 or 4 years before the owner decided to sell.
You need to find one that goes out on trips every year and preferably one that has already gone on trips this year. Find one from someone who has been using it and is selling to buy another.
We bought our 1994 Brave 6 years ago for $10K. Probably put at least 10K in it for tires, suspension components, AC conversion to the new coolant, upgrades, repairs etc over the last 6 years. Mind you we do almost nothing ourselves that isn't simple so we pay a ton. If you can do stuff yourself on the engine then you will not spend so much.
But if you read threads like this you will see many people with newer or more expensive RVs spend alot more.
Why are the 90s Winnebago's good deals? Because the Chevy 454 engine can be worked on by any mechanic. No fancy Mercedes or Diesel specialist needed. No slides to break down and need expensive repair. Simple technology (no auto awnings or other fancy electronic stuff). One advantage of not having alot of electronic gadgets is less parasitic drain and your batteries last a long time for boon docking. In addition for items you want to do yourself, Winnebago has parts list and diagrams so you can figure things out. Plus there is a huge advantage in terms of previous owners on boards like this who can tell you what you need to know to solve a problem. Winnebago built alot of units and those owners are often still RVing.
Depending on what work the previous owner has done you will need to look at the following items.
Roof air, original or second version? (Ours was second version so still going strong)
Rubber fuel lines replaced if not already done.
Dash air may need conversion in the near future to newer coolant if not already done. Our dash AC needed this a couple of years ago.
Check date code on tires and spare. Want something 7 yrs or less but probably won't get it in that price range. Prepare to buy new tires.
Inspect suspension components. We replaced all ours, shocks with Bilsteins, idler arms, sprayed the green tire goo fix it in the shock absorber air bags, bell cranks (I think)
We had to replace the LP leak detector, fire and CO detectors (easy to do ourselves)
Have brakes thoroughly checked out, bled etc. Have replaced master cylinder.
But none of this stuff is that bad because of what you are getting. Basically a motel room on wheels. I still pinch myself that the water pump, furnace, hot water heater, AC, etc all work and we got it for such a cheap price. Ours also drives like a dream compared to others we test drove. The first owner was a police office and I think it was used for stake outs and such. The second owner was a supervisor for a mechanics garage. The had taken it to Yellowstone the week before we bought it. Even so there was a laundry list of things that needed done when we bought it including generator service, change out of the sewer valve as it was leaking (easy to do yourself) plus some of the work I mentioned above. Some we did in the following years.
We haven't hesitated to take it all over and from what I read on the forum it has been pretty trouble free compared to many.
One thing we like is that it is narrow bodied compared to current RVs and that we can park it in two parking spaces across. This makes it easy to not tow a vehicle and take it sight seeing in the national parks.
If you want a real world look at one owner's experience we have tracked most of our trips in our blog. We also discuss our impressions and chronicle the repairs and improvements we've made.
The adventure started here: