Sell recent purchases to prepare for crash?

[Mark Oliver]

I bought a house (family home) in Marin County, California, in 2014 for $775k.

Now worth $1.1 million.

I owe $585k mortgage on this property.

A few months ago I bought another property for $315k - it's a vacation condo in Lake Tahoe for personal use and is also used to rent out (vacation rental). Payments on this property are around $24k per year (this includes payments on a $70k equity, taken against my first property). I get about $14k in vacation rental money per year from guests.

I have about $25k in savings, not including 401k.

I now want to become a property investor. I'm looking to buy & hold around 100 properties eventually. (i.e. Rental properties that produce cashflow).

Considering that there is a high chance we are at the edge of a crash, and considering that I bought most of my property fairly recently - should I sell my first property, wait for the crash, then buy & hold some other houses/condos?

[Alexander Felice]

If you only had a few bits of information:

When will there be a crash? How long will it last? How will it affect the housing market (specifically In your area), and what are you going to do with the money in the meantime?

My personal recommendation is to strategize with risk mitigation in mind, not capitalize on potential market changes.