Got property and good amount of equity but dont know next step

[Paul Guimarin]

First off, thank you to all the people that share the info you've learned!!

Ok so here is my story so far.  I bought a house for 141K that needed tons of work but in great neighborhood.  Worst house in best neighborhood kind of deal.  Lived in it with my wife and 3 kids for 6 years now and fixed it up little by little.  About a year and half ago we pulled 60K out with a cash out Refi.  We bought a dated condo and spent 3K(from savings) updating it, its now worth around 80K and is cash flowing around $350 a month through vacation websites(its very close to the Kennedy Space Center).  My primary house has appreciated and is now worth about 320K.  Also, I've saved about 10K I would be willing to use for investing again.

I really want another property but don't really know where to go from here.  Could definitely use the advice on what my options are.  Should I use the main house again and buy something small so I only have that 1 loan, or pull 40K(ish) from the condo and use it as a down payment thus getting 3 loans in the process?  I feel like I'm at a crucial step and would really like to make a good decision.  

Any advice and or opinion would be greatly appreciated!!  Oh and hope Im posting this in the correct section(still kind of new here)

Thanks,

Paul