Holiday Rambler is a good brand. The company was bought by Monaco a few years ago, but they've kept the HR line of products. Monaco appears to be doing a good job of supporting older HR coaches at their service centers.
At least one of our staff has a Holiday Rambler Endeavor LE, and I'm pretty sure they've been happy with it. Maybe they'll see your post and reply. I've been inside it many times and really like the layout and quality of workmanship.
We've had our 1997 Endeavor LE for over 9 years and it has given us good service. Very few problems and those we did have, HR took care of, some even after our warranty was long expired. However, we have the Freightliner chassis and Cat engine and I believe these items are a big factor in the reliability of our motor home. Newer Endeavors are built on the Roadmaster chassis and use Cummins engines. I'm not sure what was used in the 1999 models.
As with any manufacturer and models, you can get lemons, but I hear fewer problems about Holiday Rambler products than about most other brands. Do your due diligence as you would on any used RV and hopefully, you'll avoid the bad ones that are out there.