Classic Rock 98-1 looks like it will stay with Blackburn Radio. 

AM 800 CKLW has been at or near the top of Windsor's rating since the 1990's. 

I have a feeling that 580 CKWW will switch to an Ethnic format in the long run. I just don't know when.

I am keeping an eye of what happens next in London. I will not make a prediction this early. 

WHND was still Honey Radio when I heard it in Goderich in the 80's. They began as WMIC Monroe in 1956, which is why CFOS has a null to the Southwest. 
CKGL has a very strong signal into its intended market. Head to the south and both the limitation and the interference from WKBN is evident. CKGL gets weak very rapidly, and WKBN can be heard.

WRDT is on one of the HD streams that 103.5 WMUZ-FM airs. It is either the HD-2 or the HD-3. Most people in the listening area would be unaware of that.
580 CKWW has no FM assignments that they could move over to unless one of the existing Windsor stations shuts down.
The Kitchener station on 570 is News and Talk meaning that the CRTC will not allow them to move to FM. 

The statement that no broadcaster chooses to be AM only is true. They often remind people to stream them online.

I checked that signal in Sarnia. It is close to 1030 WKEG and 1310 WDTW as far as strength and clarity. Thunderstorms are interfering. The signal into Windsor and more than two thirds of Metro Detroit should be fine. If they could use more than 125 watts from that site in the future, they would need the Monroe towers anymore. That's because Ferndale is centrally located. 

It sounds like it will begin shortly. Right now the 89.3 / 94.3 / 95.1 transmission is temporarily shut off. The online stream is still on, and 630 AM could stay on for up to three more months. CFCO also will no longer need to use 92.9 FM in Chatham anymore. 

Both of my records happened away from home. 1150 CKOC Hamilton came in on a portable radio up in Fort McMurray, AB one night when it was Oldies. On FM I heard Texas near Brantford. That was in 1993. One of the stations I remember hearing was the main Z-Rock signal on 99.1 FM. The was before CBC Radio One moved from 740 AM to 99.1 FM. 

HD Radio is too low powered compared to regular FM to have good coverage. WOMC Detroit easily exceeds 120 km on regular FM when you head towards London on the 402. The HD signal starts breaking up right in Sarnia which is about 80 km from Ferndale, Michigan. 

That is actually a good question because signal drop outs have always been severe on AM HD radio stations. During the daytime CHLO is 10 watts digital. The closer to Ashgrove (near Georgetown) you get, the more solid the digital side of the broadcast becomes. Their daytime power is higher than their night power in both standard AM and HD. It always takes a few seconds for the digital to decode. 

A very limited number of former AM only stations in the United States now use the 100% digital mode without the analog. These are supposed to be technically superior to the hybrid broadcasts. 
 

Did they attempt to steal copper? That's what happened to the former CKCO-TV-3 (channel 42) site in Lambton County a number of years ago. 

It would still be KX Country. 

Many AM broadcasters changed dial positions over the years. Here are the Ontario stations from about 1950 to now.

CBEF : 540 to 1550  Windsor 
CHYM : 1490 to 570  Kitchener*
CKTB : 620 to 610  St. Catharines
CFGM (a) : 1310 to 1320  
CFGM (b) : 1320 to 640  Richmond Hill
CHFI : 1540 to 680  Toronto
CJRN : 1600 to 710  Niagara Falls
CKGB : 680 to 750  Timmins
CIAO : 790 to 530  Brampton
CHAM : 1280 to 820  Hamilton*
CFTJ : (a) 1110 to 1320
CFTJ : (b) 1320 to 960  Cambridge
CKKW : 1320 to 1090  Kitchener
CKJD : 1250 to 1110  Sarnia*
CJMR : 1190 to 1320  Mississauga
CHWO : 1250 to 740  Oakville / Toronto*
CHLO :  680 to 1570  St. Thomas / London
CHNR :  1560 to 1600  Simcoe
CKEY :  580 to 590  Toronto
CKSL :  1290 to 1410  London
CFOS :  1470 to 560  Owen Sound*
CKDO :  1350 to 1580  Oshawa
* = vast improvement



 

It's starting to look like HD could become the next AM Stereo (not in a good way). In the U.S. they are now testing radio over ATSC 3.0 UHF signals. 

https://www.radioworld.com/columns-and-views/guest-commentaries/atsc-3-0-audio-services-the-how-and-why

On paper it appears that the coverage of the Michigan test beats all of the HD signals. WOMC-HD-1 and 2 breaks up in Sarnia as you drive. I have heard WOMC's standard FM broadcast in the London area many times. 

CKWW will need to go more in a News and Talk direction before it will work in Windsor. The only AM radio music format the worked in that market from the mid 1980's up until the 2000's was Adult Standards. CKWW remained Oldies for years because it was Windsor-Detroit rather than Windsor only like what both the current CKWW and 1960's to 1993 version of CKWW was. 
 

At night you could try these in the GTA / Southern Ontario
(1)  680 News
(2)  AM 740 / Zoomer
(3)  770 WABC
(4)  1030 WBZ Boston
(5)  1060 KYW Philly
(6)  1150 CKOC or 1220 CFAJ

Locally where I live.
(1)  580 CKWW Windsor
(2)  AM 800 CKLW Windsor
(3)  News Radio 950 WWJ Detroit
(4)  1030 WBZ Boston
(5)  WTAM 1100 Cleveland
(6)  1380 WPHM Port Huron