I’d have to agree with Harvey and recommend you go for it based on your “forever” comment. I think the timing will never be absolutely perfect. If prices are low then rates are higher if rates are low prices tend to be higher so there is always give and take.
As far as the condo…I really hate to disagree with Rich since he’s probably waay smarter than me, but I’d probably keep that too as an investment if it’s in coastal SD as long as it’s breaking even. I’m still curious what rents might do with this correction that seems to be coming at some point. My gut says that as long as demand stays strong if prices did start to fall then rents would get even more crazy from a demand standpoint because less people would be able to or want to buy. With more people choosing/being forced to rent it would push prices up (my opinion of course). The only curveball in my opinion is if demand starts to fall due to some circumstance. Could happen I guess, but does not seem to be happening now or anytime in the recent past.
In addition to my belief that rents might increase over the next couple years regardless of prices I’m not sure where I would put the money if I sold. Say the rents go up only 3% per year (past few years have been waay more than that as you know) then at least your keeping up with inflation. There was some talk about daycare and kids and maybe the cash flow from that condo ends up paying for one of your children’s college education someday 18-20 years from now in exchange for managing the property until then. Then when they are done with college it goes back to you each month.