Should I stay or should I go!!!???

[Sean Mamola]

Hi guys! I love love this podcast and forum, got hooked on it by the rental rookies! I drive an hour each way for work and am sparked up for investing. I need some guidance though- like real guidance- I have an investment property that I bought for 255k 3 years ago- and now can sell for 360-370 (My renters are highly interested in buying the property.) My loan is at 207k now. This is a small community that has held strong through the toughest of times However, I think it is definately topping out at this price. Plus 200 acres of land was just purchased to put up 800 new homes in this Mayberrish farm town. Here are the obstacles I was hoping I could get some advice on- Because of you guys- I want to grow my property portfolio and create financial freedom for myself. I am 43- retired broadway dancer, and have waited tables for income all my life. I love what I do- I just don't want to be locked into it for the rest of my life. I now realize that I an amateur in the game, but no less, in the game and have the potential to amass some more properties and basically want to set the blueprint for future purchases.

So- my father passed away in October and I made the conscious choice to leave a company I was with for 18 years in NYC and nurse him through his transition in CA. Since then I have had to start with a new company at almost half the income. I am interested in moving North, closer to remaining family and a new and upcoming market because of a trillion dollar sports arena being built right in the heart of downtown. I feel the growth in this market has more potential. I'm lost when it comes tot he decision of keeping the investment property where I have negative cash flow but heavy equity( I pay $50-$100 a month out of pocket)- or selling it and buying 2 properties, 1 owner and 1 duplex-or do I keep the investment property and try a HELOC for 1 owner occupied property (Obstacle being new job and 1/2 income) Plus I am 43...the thought keeps creeping in my mind "is it too late for me to be doing this? I am a single man with great credit-a Nice 401k-and an investment property- am I crazy?"