@Account Closed I have recently been faced with a similar situation and I decided to sell. As everyone will tell you, “it depends on your personal situation." The problem is no one has a crystal ball on what appreciation is going to do in the coming years. San Diego is probably a good bet on continuing. I was holding on to a condo that I purchased in 2000 as a primary residence and began renting it out when I moved on to another property. It made minimal to no cash flow but it was in great area and I knew in my gut that it was going to keep appreciating and it has. I’m at a point in my life now that I want cash flow. I would like cash flow to at some point allow me quit my W-2.
Finding Bigger Pockets last year opened my eyes to all the other options I have to make that equity work for me. Would my property keep appreciating? Likely, especially since a metro stop will be two blocks from it in two years. I still decided to sell because I wanted more control over my money and not to rely on speculation. My big issue is I'm very busy with W-2 and family. In addition, the market I live in (Northern VA) is tough for buy and hold. I sold the condo earlier this month and I'm doing a 1031 exchange into some out of state turn-key properties .Once those properties close, I plan to refinance and take most of the money out of the properties and start on building a team closer to home (likely Baltimore) to purchase more properties. I went the turn-key route because I didn't want all the stress (it's still stressful) of finding replacement properties in 45 days especially since I don't have a good team built up anywhere.
Hopefully my situation may be of some help. Best of Luck!