With condos instead of budgeting for major expenses like roof, ext paint, landscaping etc the association takes care of those and you pay the maint fee instead.  

After he was finished with the roof and gables he sent us a bill for and extra $13k and said he could not have forseen the condition.

$40k does seem low for needing two kitchens, labor, roof, permits etc.

@sean @Sean Autry you would think that people with children would be more self aware and give more credence to keeping a roof over their heads, but alas this is not the case.

Would I be relatively safe looking for issues on my own such as leaky roofs (stained ceilings), foundation cracks, drywall cracks, and poorly executed remodeling? 

The house is from the 30's and it looks it will need quite some work (roof, bathrooms, kitchens, refinishing floors and siding).I was wondering if anyone can refer me to a reliable and honest contractor in the area.Cheers!

Could also be the damage you noticed on the roof while looking at it from the backyard or moisture you saw under the kitchen sink that "could" cost a lot of money to repair.

As long as there are people in your market willing to stay in 3-4 unit houses, that's they way I would suggest. 3-4 streams of income and 1 roof, 1 foundation, 1 yard.

it's really difficult to tell you every single thing that i look at. i have lots of experience so i can just make offers based on the listing pictures. even if it's just a single picture of the front of the house. that's cause i buy similar houses and know about how much it would cost. but i have a lot of experience, so nothing phases us.in addition, when you have a checklist, the agent will know you are not experienced and will question your ability to close. big things are - kitchen, bath, electrical, roof, concrete.the rest is child's play.good luck.

Whenever I need to pay property taxes, or replace a roof, ect, I would draw from that account.