Buying in a Seller's Market

[Luis Pineda]

Hi All, 

I have recently been looking into buying my very first property ever. My plan is to use my VA home loan benefits to purchase a condo, since the prices of single-family homes are incredibly high, especially here in San Diego, and then after my year of occupancy rent it out and purchase another property. My concern is that if I buy in a market where prices are high, will I potentially lose money if housing prices drop?