The only people to have lost money on financed San Diego buy n hold RE are those that sold when the market was depressed (mostly people over leveraged).  

Keeping Bill Gulley well spoken caveats in mind, the annual average of the Dow Jones from its 1929 pre-Depression zenith to today (sort of a worst case scenario) is a 4.42% annual return.

You could purchase this property and come across a positive cash flowing deal tomorrow and feel like the world's depression came crashing down on your shoulders.

If times get bad, or if I went for the depressed neighborhoods with slight negative appreciation, then the advantage of mass leverage gets wiped out.

Johnny "I KEEP FINDING DEALS," George "MY CAP RATE IS 20% ON EVERY DEAL," and Frank the Depressed Real Estate Guy " Don't do it, I lost my shirt, stay away."

@Kyle RobertsonIt’s been a year now self employed and it’s been messy, hard, semi-depressing at times, small moments of questioning myself —- done in a pandemic... a lot of crazy highs and lows and emotional roller coasters... some of my greatest single-time paychecks and some stretches with with almost nothing... having a bad@$$ wife helps a ton as she went back to work for a while to support me...

Which will be key when you transition to buying depressed properties, because getting VA loans on them are more challenging but not impossible.

I'm Bryan O'Neal and I'm a residential contractor in a really depressed market.

I am actually not depressed about the situation. 

Working with my Marines through debt management, financial problems, family problems, allegations, substance abuse, and severe depression are mostly learned informally on the job.