Covid-19 may send up house prices in areas where rich city dwellers want to move to during the pandemic, but other areas will be unaffected. Poor areas will get poorer due to increasing unemployment which will eventually lead to lower house prices there.
Timing the market is not that hard. I sold my previous house in mid 2007 and bought my current one in late 2009 (after house prices had dropped 20% in this area). Getting a mortgage to buy during a recession can be a problem though. Also, the boomers pulled the HMO ladder up after them. In many areas you now need planning permission to set up a HMO and the local NIMBYs hate students and poor people so that is usually impossible.
Many HMO's in Crewe were bought and developed by Eastern Europeans. I do not know if they qualify as boomers but the areas are pretty rubbish now for long term residents.