Next, the commute. What's more important to you, the time& money for the commute, or the driveway/yard? Single family homes do require maintenance & repairs on a regular basis. Condos have less that needs to be done by you, but you're paying for it with your HOA fees.
Are you anywhere near retirement? Now is such a good time to buy, would it make any sense to buy out of the City and rent it out, saving it for you to move into after you retire?
Pacific Union RE
The best advice I can give is that you should buy a property on if you want to live there and if you can afford it. Then check your gut.
If it doesn't feel right, it won't work. If you feel happy and if it feels like a home ... it will probably work out.
You can minimize your risk of buying a "lemon" of a house by having it inspected - your Realtor should make sure there is an inspection contingency in your offer. And there are homeowner insurance policies that cover the mechanicals for the first year - you could ask the seller to buy one for you, or do it yourself.
Congratulations on your looking into the financial picture before you make a commitment to buy - it's a wise move. And best of luck in your search for a new home.