The two investors I knew growing up kept at it their entire lives. Here is an article about a local Portland guy that is a legend in RE. Do you plan on investing forever?

Joe Weston unplugged
Published: Monday, November 19, 2007, 8:21 PM Updated: Wednesday, November 21, 2007, 9:35 AM
By Ryan Frank, The Oregonian

I had lunch Monday with Portland's 69-year-old godfather of real estate, Joe Weston. Weston has been at it for decades. He owns 2,500 apartments and industrial and commercial property across Northwest Oregon. He also remains the controlling interest behind the Hoyt Street Properties. I love this job because the real estate industry is full of personalities. Joe Weston is one of the Old School guys. He's worked in the same aging office building on NE Broadway for 40 years. The building happens to be a short drive from where he grew up at 31st and Flanders. At lunch, Weston wore his trademark red, white and blue tie with bald eagles.
Weston is traveling more these days but he remains busy as always. A quick run down what's on his to do list:
- Hoyt Street still has two blocks left in its current Pearl District phase and a whole other phase to follow. They're working to get more height bonuses from the city. He says sales are "extremely slow" at the Encore, his current project under construction.
- Weston is now doing some projects on his own. Benson Towers was the first. The Cosmopolitan in the Lloyd District will be next. He has OK'd the Cosmopolitan through construction documents. He plans to shelve the plans, then restart the project when the market returns. Weston pushed the Cosmopolitan ahead of another condo, the Manhattan. The Manhattan had been planned downtown just west of I-405. "Why did I reverse? It has smaller units and when the market comes opens up it will at a lower price point," Weston said. He plans to serve Lloyd District workers and people who live elsewhere but have a second home in the city.
- How long until the condo market returns? Weston says it will be "at least two years."
- Weston has a small place in NE and another place near Oregon City. "I don't go out there too often. Gas is too damn expensive."
- Over the last five years, Weston has purchased a bunch of land near 12th Avenue and Sandy Blvd. His holdings are now equal to 20 city blocks or about 800,000 square feet. "What am I going to do with it? Damned if I know." Weston likes the property because its platted for superblocks -- 460 feet long instead of the standard 200 feet -- that make it easier for development.
- He's also bought hundreds of acres near the Scappoose airport. He's in talks with the city of Portland for a new a police/fire training center, Mayor Tom Potter's big project.
- Weston moved across the river to buy about 73 acres at 192nd Ave. and Highway 14 near Camas. He said: "Vancouver is no longer a bedroom community of Portland, Oregon. It is a city unto itself."
- Weston says Central Oregon's market is dead, dead, dead. He sold much of his land and owns only two big lots in the Broken Top Highlands.
- In California, he owns about 78 acres in Palm Springs that he's developing for housing lots. "The nicest lots in Palm Springs."
Clearly, Joe Weston is not retiring any time soon.