I’ve come in late on this conversation - and I have been lucky with real-estate to date.
Rented for 5 years in school and working, then…
First house, bought in 1996, $145K (Maryland, 3br, 2bath, 1700 sq. ft., 2 car gar., .8 acres) + a free .75 acre adjoining lot that was overlooked by the seller’s children (estate sale) and prompted my quick purchase! I gutted the entire house, renewing everything, putting about $100K into it. Sold it in 2007 for $399K. Also sold the adjoining lot in 2008 for $150K.
Second house, bought in 2007, valued at $750k, BOUGHT IT FOR $500K (a relo deal - I knew when they were starting to offload and threw in a lowball) (Maryland, 4br, 5 bath, 4000 sq. ft., 2 car gar., 2 acres). We took a beating like everyone else between 2007 and now - was revalued this year at refi for $615K, I’ve put about 10K in it, so still ahead of the game.
In 2010 we took advantage of the market, buying back the lot we sold (for far less) and buying a condo (another estate sale, a classy condo complex in Maryland) for about $60K under market value. I put $10K in renovations into the condo and it is leased as a revenue stream. We also might build on the lot and lease it out until the market comes back.
The market is still good in some areas, and took little beating in those areas (Maryland is one of them) over the last 3-4 years.