Our home has recently sold and we are under contract to cash purchase an un-zoned lakefront primary residence with 8 acres, of which 5 acres are flat and cleared. 

@Tyler PsenicskaYou can also look at doing a flat-fee MLS listing so you still get maximum exposure on by being on the MLS.

., tenants working form home = higher maintenance and bills vs tenants' income likely staying flat)

Wife and are finally getting ready to pull the trigger and we're are looking at a two flat.

Should I ask the other tenants or just flat out reject the request?

I've been keeping an eye on that market and it looks like it's been relatively flat since pre-covid, given that it was one of the hardest hit by it with so much international travel involved.

Dang @Stephen Foltin, that sounds like a frustrating ordeal altogether!

The majority of single family homes in the district can be converted to duplexes (two family flat) or can have legal ADUs added, but the distinction depends on the underlying zoning.

The forebarence is one issue, but another altogether is the fact that new construction is lagging MASSIVELY compared to where it was AND compared to where it needs to be in order to satisfy the difference between demand and supply in many markets, meaning as interest rates continue to be down and demand continues to be up, it is unlikely that we will significantly push the market back to being a a"buyers market", or even back towards being balanced, for several years.Add to that the fact that our GOV does not seem spine-full enough to put stimulus or tax breaks towards builders to subsidize the hair-raising cost increase of builds in any massive way, but continues to thing helicopter money is a good idea. 

I'm a new investor looking to acquire 2-4 flats in Chicago's northwest neighborhoods.