I skimmed this thread and have a few thoughts...
Construction timeline:
If you own a property and it came with permits, etc. you may be able to go from greenfield to built in a year. But as soon as zoning, conservation, tricky drainage, etc. comes up, expect delays to push past that timeline, but yeah, from hole in the ground to house can be pretty quick, especially with a canned plan.
For a development, the process from Farmland, rezoned to R1 residential, through plan of subdivision to siteplan approval, to development charge bylaw, to engineering review, conservation review, environmental review, council approval, grading approval, and finally development will take about 5 years in my municipality. And the developer is competing with 20 other guys for the attention of about 5 reviewing staff in my department, so yeah, there's bottlenecks along the way. If there is a historical/anthropological element to this, double that timeline at least. Some developments I worked on 18 years ago are finally being built now.
Regulatory costs:
Single family homes are sucking cities dry. While the review/approval process takes forever and is fraught with delays costing developers big time, the construction of new single family developments is having the same effect on the tax base where new development is taking place. The linear and social networks that connect our neighbourhoods - including roads, water, wastewater, stormwater, electric, communications, parks, schools, community centres, etc. along with the ongoing maintenance of those networks is not borne by the development, but by communities as a whole.
We try to transfer the lion's share of those costs to a developer in the form of development charges and land dedications, but ultimately the development costs are never fully borne by the developments. Currently development charges in our municipality are in the order of $150,000 per SFU (shared by the town and County). These charges are passed on to the buyer by the developer. we have no other mechanism to pass along the costs to the new homeowner. Consider that a single sidewalk plow costs us $120,000, plus a new hire to drive it, shop time to maintain it, etc. ... now add on garbage, grass cutting, etc. and it all adds up.
The next progression is that the existing residents will invariably demand that they not be strapped with the costs of a new development and that the "new people" pay their own way and you get politically motivated skyrocketing DCs and simultaneous tax freezes resulting in a high entry cost to the community and existing services being funded below inflation - at a net loss when you consider the purchasing power of each tax dollar. And sometimes the residents want centerlines (inside joke there).
Value of a dollar
On a more personal side, I try to remind myself that a dollar spent today is $1.05 tomorrow, or $1.25 in 2 years, etc. The buying power of your down payment is decreasing each year you stay out of the housing market. Personally, the $400K that was an absolutely ridiculous amount to spend when we moved into our suburban home 10 years ago now buys a run-down Semi an hour and a half out of town. Even the best years I've had in the ETF game have not kept pace with the rising cost/value of real estate. Now I know there are dozens of hidden costs with maintenance and depreciation and utilities and selling fees and capital gains taxes, but I don't think the stock market is keeping pace with our real estate buys. And that is just because of the time-value of money. Inflation will always make the cost of a house a year ago the best deal you can buy.
If the market does correct/crash/burst/flatten, the simple mechanic of inflation will pull real estate values out of the dip and bring them back to reality. Unfortunately the same cannot be said for working wages which is what will bring on the crash if it happens. Today the RE market is ballooning above what rents can support speculators and what buyers can afford in a mortgage. The correction needs to take place both on the income side and the cost side before we even start talking about mortgage rates and interest.
Anyway, this is already too many words so I'll tap out, but this is a fun subject to speculate on, and yeah, development and real estate is full of tough questions and tougher answers right now.