The owner will maintain insurance on the property. 

What is the best choice over the life of the investment...and more importantly, which one brings you less stress to manage and maintain.

Apartments are well maintained, all electric, newer floors and central and in an ideal location for renters.

I'm planning on buying an investment property as soon as 6-9 months and would like to maintain a good relationship with my realtor and his connections.Thanks so much for that advice. 

You open yourself up to a lot of liability as you are responsible (at least in Maryland) for maintaining existing utilities and are then responsible for their payment.

I would recommend a value add play on an existing poorly managed or maintained apartment complex.

LLC's are easy to create and cheap to maintain.  

At first i was thinking two 3 family homes and just live in one collect the rent on the other 5 apts and just set aside enough for expenses(taxes,utilities,maintainence) but then i got to thinking i do want a family someday and id like to own a chunk of land.

In fact, it can definitely be the best choice when maintaining a yard or bearing the expense of interior maintenance is not practical.

There are many nice homes for sale that would earn a well as short term rentals but have a harder time maintaining a good return as a long term rental.Lastly, when looking at condos and townhomes pay close attention to the condo fees and the financial status of the condo association.There is a rental analysis sheet in the Bigger Pockets file download section http://www.biggerpockets.com/files that would a good start with analysing the numbers on target properties.