Selling our Condo or House to reinvest into a multi family... what say you?

[Demian Sims]

Hello all,

 So we are in a rather good situation but would love to improve it by getting more revenue streams from rental properties. Our situation is that we purchased a condo at the height of the recession for 224,000 and it has appreciated to more then double that. We currently rent it for a positive cash flow of 1100 dollars over the mortgage(and all other expenses). So a year ago we took a Home Equity loan and purchased a house for 525,000 that has now appreciated in a year to 660,000(as of our refi and last appraisal). We would love to invest in either a duplex or triplex but struggle with the best method to make it happen. If we sold the condo we would have close to 300,000 in equity but would lose a positive cash flow. Selling the house would get us much less equity to work with but the house probably couldn't be rented for a positive cash flow YET. So thirdly would be somehow branching into another property without selling either, but that may be risky and impossible with standard loans. Any suggestions would be really appreciated. We are new at this and have a young family that is growing out of the current house.  Thank You, Demian-