Should I Sell My First Home or Hold It? SoCal VA Buyer Transitioning into Trades — Ne

[Roberto Lopez]

Hey BP community,

I’m looking for some seasoned SoCal investors to pressure-test my thinking. I’m 26, married with a newborn, and currently weighing a major decision about whether to sell or hold my first property.

Here are the specifics:

Primary Residence (OC):

• Purchased for $850,000
• Current mortgage: ~$6,400/mo
• Estimated rent for full house: $3,600–$3,900/mo
• I also have one roommate (a friend) renting a room, helping offset some of the payment ~$1,100/mo
• We planned to convert the garage into an ADU, but we don’t currently have the funds and the project feels overwhelming with everything else going on.

Current Life Changes:

• Transitioning from active duty Marine Corps → IBEW apprenticeship (Local 11 or 441)
• Newborn at home
• Career switch into electrical trade
• Refinancing in January with a VA IRRRL
• Planning to move out next year and rent the house, BUT the negative cash flow concerns me

My Goals:

• Build long-term wealth through multifamily
• Use my VA loan strategically
• Start accumulating properties over the next 5–10 years
• Balance family, finances, and career in a realistic way

The Dilemma:

With the numbers where they are, renting the house means going negative each month unless I finish the ADU (which I can’t realistically fund right now). Selling would reset my finances and give me capital + mental bandwidth, but I don’t want to walk away from a strong appreciation market prematurely.

I’ve been analyzing areas like Whittier, Downey, Long Beach, and San Pedro for my next house hack or 4-plex. But I’m genuinely torn on whether holding this first property even fits my long-term strategy anymore.

My questions for those who’ve been in my shoes:

1. In SoCal, when does holding a negative-cash-flow property make sense?
2. Has anyone regretted selling their first home early?
3. For those who transitioned into the trades, how did you balance cash flow vs long-term appreciation while your income was growing?
4. Would you sell, clean the slate, build reserves, and then target a 4-plex?
5. Or hold the property, let it appreciate, and deal with short-term losses?