Looking for Direction

[Tim Sughrue]

I've saved a decent chunk of change (enough for a 10% down payment on a $300,000 house with a few thousand left over). I've been looking for about a year and after almost purchasing 3 of the first 6 houses that I looked at, I realized that this purchase is TOO BIG to just buy anything. I have also realized that I have absolutely no clue what I want, literally no clue. I feel the pressure to buy because the market is so low and I am told it will most likely start building up again soon. I essentially want to be able to sell my purchase for more than I bought it for, but I don't want to tie up so much of money that I am barely getting by after my monthly payment. So $300,000 is my absolute MAX purchase and that is pushing it.

The problems I am realizing is that the more I search I've noticed that houses under 250,000 in my area have major flaws such as location and/or unfixable architecture (mostly tear-downs). My family is extremely handy when it comes to fixing/remodeling houses so I definitely have that on my side, what I don't have is the bankroll to make it happen in a hurry.

On the other-side of real estate I have been researching condo's which seem to fit more of my immediate living needs (location, cost, and comfort). The typical condo close to boston which is the more desired location in the area goes from anywhere between 150,000-250,000. If my main goal was to just live in the moment for now and see what happens later this seems like a no-brainer (buy the condo). The problem is, I want this purchase to eventually carry me to the next stepping stone towards my life goal of being a real estate entrepreneur.

My family members tell me that condos are bad investments and you have condo fees and blah blah blah. (I'm hesitant to solely listen to family because I feel they have bias opinions based on what has worked for them). Maybe this is true, I'm not sure. Which is why I'm hoping someone can give me some direction on how I should go about this purchase.

P.S. I'm currently searching in the (5-20 minute) range from boston.... I could go a little further out about (30-45 minutes) and can get a far better house for the same money but these areas aren't as desired by buyers and my commute would be longer..

Thanks in advance for your responses!!!!