@Ankur Bagchi I think it is always a good
time to buy if the deal is right, which mainly depends on your goals. Will the other room rent cover enough for you to feel comfortable with the deal? If you rent out your room after moving out, will the property expenses be covered? Some invest for appreication, but I’d be careful with negative cash flow deals.
The main downsides of a condo purchase is HOA control, for example, with a special assessment, they can ruin a deal. The HOA fee will go up every year if manages correctly, so expect increases on fee expenses. Other downsides could include parking and sharing walls with others. The upsides to a condo purchase include not having to bother with landscaping or structural fixes. Also, sometimes the utilities are covered by the HOA, so less time dealing with utility companies.
When buying in a city, I’d check migration trends and rental regulations, as well as taxes. Hope this helps!