Hold or Sell 2 Properties?

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Hey All,

I'm a new BP member living in San Diego, CA. I'm looking to get some advice on my current situation. I have 2 properties that I bought prior to finding BP and becoming knowledgeable (somewhat) in REI.

Property 1: SFR in Orlando, FL. Bought it without any prior real estate knowledge.

• Purchase Price: $239,000 w/ 20% down (about $50k) 
• Current Rent: $1650.00 
• Mortgage: $1215 + $100/month for lawn
• Monthly CF w/o maint. issues: $335
• Current Home Value: $250,000

Property 2: SFR (Condo) in Downtown San Diego, CA. Bought it with VA loan. Was a probate sale.

• Purchase Price: $400,000 ($2,500 in closing costs) 
• Using as short term rental: Avg Monthly Income - $3,200.00
• Mortgage: $2615 + $200/month for utl + $65/month for WIFI = Total Monthly Exp - $2,880.00
• Avg. Monthly CF: $320.00
• Current Home Value: $449,000. 

I want to get into multi family apartments 16+ units. Have about $30,000k cash saved up as well. 

Any advice would be greatly appreciated. 

Thank you in advance!