Your question reminds me of HGTV and the kinds of decisions that their couples are always having to make. Let's assume you have found two residences, one a 1 bedroom condo in downtown Boston, and one a single family home just out of town on Rt 128.
Your question asks for the wisdom in choosing one over the other. And I answer, what's right for me is not necessarly right for you.
Here are some things to evaluate which might direct your thinking.
First of all, a condo is an apartment that you own. Meaning that you will recieve a deed for the property and with it will come certain bylaws, rules and regulations. Read them before you buy. You will learn what you will own, and what you can and can't do. You will also learn what the monthly fees are and what the taxes are.
I have lived in a one bedroom condo in downtown Boston. It's pretty cool. Nice to walk to restaurants and get a coffee and a paper just downstairs. My opinion is having a car in Boston is an expensive luxury, but not one I was willing to give up. Parking was very expensive--even monthly in the Common Garage. So unless your condo has parking, remember parking will be extra, and doublely so if your girlfriend has a car too. And car insurance will sky-rocket.
Also I noted that garbage in Boston is collected about 4 AM almost every day by huge trucks that lift dumpsters way up in the air and everything spills out into the truck--CRASH. From my windows I could see into a few dozen other Condos and apartments, and looking down I could see the dumpsters--let me assure you there was not much privacy and it was noisey on Beacon Hill.
In a house you will not have the condo fees, and you will have the rights to make changes and modifications if you so desire. Parking should not be as much of an issue and you might actually have a garage. This would mean that so-called boy-toys like a boat on a trailer or a motorcycle could find it's way into your posession for weekends and down time.
So you will have more privacy, fewer neighbors and probably a lawn and garden and you will be responsible for all that, so the savings on the monthly Condo fees could be used up if you pay someone to mow the lawn and shovel the snow. If you are handy, you can do it yourself. And you will have the excitement of a daily commute. Plan on leaving early in the AM and getting home whenever.
Once I moved out of the city, I missed the freedom of no-commute and the option of Boston after-hours. Sure, you can drive in and you'll have the car for the ride home, so you can stay late, but your decision needs to take this into account.
Getting back to your question, which is wizer: the condo or the house? It depends...
Hope this helps,
Real Estate Professional