I found a lot of places even for under 400K in Santee area:

http://www.zillow.com/homes/for_sale/Santee-CA/house_type/16876333_zpid/6943_rid/3-_beds/2-_baths/0-400000_price/0-1481_mp/32.904956,-116.898222,32.813391,-117.078467_rect/12_zm/1_fr/?view=map

Now if you can get a sailboat under 30′ then slip fees are doable at 500/month:

http://www.harborislandwest.com/slip-rates.html

I plan on a 25′ Catalina sailboat with two heads and two cabins with galley. That puts me at under $400 for slip fee. So factor a $3K mortgage plus $500 slip fee not too bad for best of both worlds.

Actually since I am also a pilot, I’ve looked at buying a home outside of California in place like Nevada, Arizona or Oregon where prices are even cheaper!

So a plane at 80K plus sailboat at 10K plus home in OR/NV/AZ at $200-300K that makes a monthly nut of 3-4K to have all toys accounted for and tax breaks for business. Or live in cheaper part of California like Chico or Oregon coast.