I live in a one-bedroom condo. I actually wanted a two-bedroom, and in my MCOL (lower than San Francisco and New York, more expensive than Lincoln, Nebraska) city, (in which real estate costs were rising fast, although they seem to be stabilized at the moment), a two-bedroom condo in a well-kept-up, relatively new complex that was also a reasonable commute was beyond my budget between the initial mortgage and the larger monthly assessment. My decision wasn't really about investment value--I needed to get out of my (poorly-maintained) apartment and with an incandescent rental market due to a shortage of units, I decided buying was right for me. I knew I had zero desire to deal with outside or systems (sewer, roof) maintenance--the smaller issues in a condo are plenty for me--so condo vs. single-family wasn't ever a decision as far as I was concerned. I held out for a great location (in exchange for about 100 sq feet less than the average footprint) and lucked into a very solid HOA. I am very happy here and it was exactly the right decision for me. I will be here until I move or retire, unless something about my life circumstances changes (ie, getting married, or a handicap that would mean I couldn't use the stairs.)
Based on my experience (looking at the low end of a hot market)...start looking at one of the real estate websites well in advance. (we have a city one, but there's also Zillow, Redfin, etc). By the time I came to buy, I knew exactly what complexes were in my price range in my area, and which ones constantly had units on the market. When a unit came up in my complex, which was uncommon at the time, I knew to jump on it. Be cautious of complexes with really low monthly fees (which probably means they aren't putting enough in reserve) and really small complexes, because if you have one rotten neighbor it messes with the HOA. Also, if you are in the U.S., complexes with more than 25% of the units rented out are harder to get mortgages in. One thing you might consider is that one-bedroom condos can be appealing to downsizers, but you have to think about accessibility (ie, no 3rd-floor walkups.)