How to start investing income property with proceeds from a home sale?

[Emiliano Dias]

Hello all,

I have a penthouse condo in downtown San Francisco.  I'm thinking of selling it and moving back to the east coast (southeastern Massachusetts.)  My realtor wants to list my condo at $750,000 which would give me about $400,000 in proceeds after the mortgage is paid off.

Does it make sense to purchase a pair of investment homes outright (possibly a triplex and a slightly nicer duplex to owner occupy), or should I apply for mortgages and put the rest of the money in my savings?

I've never invested in property before, would this be a prudent method to ensure an income an a place to live with little initial effort.

Thanks,

Tony