Should I sell my home?

[Jody Tims]

Hey BPers! 

I own a 5/2 on 1.25 acres in Oregon City, Or, near Portland. I have a view of Portland and a bit into Washington. The home is unique in that it is a 1965 ranch with lots of Midcentury charms. I have about 300k in equity and the market is at about 18% a year. I am preparing to buy another home in the burbs using a HELOC for the 5% down. I'd like to purchase property #3 in the next year or so to generate cash flow. After running the numbers, it looks like I will cash flow about $300 a month once I rent my current home. The house and property can require quite a bit of maintenance, which I do not have the time to do. I was wondering what people thought about this situation and whether it might be more beneficial to sell the home so I can do the full 20% on the new place and have a down for 1-2 more properties that would generate more cash flow. I realize I'd be trading money later for money now but I'm just getting going on my real estate journey and not sure of the next move.

Thanks so much!