https://www.longtermtrends.net/home-price-median-annual-inco...
I had a front row seat to this in 2010, during my stint as a creditor's rights attorney.
It was this odd tango of homeowners who would strategically default, and creditors dragging their feet throughout the foreclosure process.
It was implied that as long as the property was sufficiently maintained, the creditors would waive the deficiency judgement when they decided to foreclose. They would try to limit the number of foreclosures in a neighborhood or zip code to prevent saturating a given areas market.
Kind of a brilliant win win. No cost living for up to 3 years for being a good caretaker. That's the only bright side to it. It was savage and emotionally taxing, I'm glad to be a debt now.
That said, if the rate is attractive and you have a long time horizon which you can predict reliably, then you might still find the rate attractive. if you plan to sell over the next 5 years though, it may be better to rent and negotiate lower rents if housing prices fall.
Alternatively, if you have a specific use for a house that requires you to own, consider whether that use is worth a premium of homeownership. (e.g. you have a woodworking business and need space that is hard to rent, or you have kids that need to go to a specific school district)
Timing the market is a bad idea, having contingencies for the eventuality that your timing was wrong is a good idea. so, build the cost of the contingencies into your model.
Finally, don't get into a false dichotomy of rent vs buy. it is better to think about the total sum on the table for either option and how you'd like to allocate it. e.g. you could just buy a smaller house, or rent a bigger one. Or, rent as cheaply as possible and buy gold, or bootstrap a small business. remember to enumerate all possible capital allocations before getting trapped in the choice between just rent vs buy.
You asked about Chicago - the city as a whole doesn't have the outrageous prices of California, and so might do something different from the national average. Within the cities some areas have better prices than others. Different areas of the city will see different results. This applies in California as well - location matters.
You have to live someplace. What will rent cost if you don't buy now. I lost money on my first house (moved at the bottom of the 2008 downturn), but after accounting for all the rent I would have had to pay instead of the house I was still better off financially.
Make your best guess based on the above. You will be wrong in at least minor details, but hopefully close enough. In the worst case you just have to accept you made the best decision you could at the time, and there was no way to know it would turn out bad.
You can't really time the market. So buy something you want at a price your comfortable with.
How can you determine if that is the correct/desired course of action?
https://www.federalreserve.gov/monetarypolicy/monetary-polic...
https://www.federalreserve.gov/newsevents/pressreleases/mone...
I think the bubble talk is slightly overstated due to the increase in remote workers. That demand isn't going anywhere soon, which means prices aren't likely to come down much. The Fed is really trying to price out AirBnb and institutional investors, which only account for a small percentage of the market anyway.
Mortgage rates are likely to stay elevated for a year minimum, so that’s just reality if you need a place to live in the meantime. Paying the extra monthly cost until rates drop and you can refinance probably still beats renting for that time.
Don't forget though that real estate is an inflation hedge so even if the market cools it is hard to see it falling off a cliff.