Yeah, I hate it when I find out about accidents because people start texting to see if I'm OK. I also have a Mooney Ovation, based at the next airport to the east.
Weather-wise... I don't know why KRYV doesn't have a METAR any more, it used to. This is the first I've noticed that it doesn't have one any more.
KUNU is to the north and a hair east of KRYV, not the south. KUES is east, KMSN is west, KJVL is SSW:
KUES 141345Z 32007KT 10SM OVC007 15/13 A2970
KMSN 141353Z 34003KT 8SM BKN250 20/13 A2968 RMK AO2 SLP048 T02000133
KJVL 141345Z VRB03KT 4SM HZ CLR 19/15 A2970
So, it may not have been as bad as KUNU.
I listened to the LiveATC archive for MSN Approach, and at one point the controller says "25C, you up?" and then a couple minutes later asks a C172 off of Blackhawk (87Y) to fly over to the east and see if they can spot anything because "I had an IFR departure from Watertown pop up momentarily, but we're not in contact." So, the turns weren't a result of ATC instructions.
One other thing to note: Watertown is very odd in that they have their FBO staff trained/certified to be able to relay IFR clearances via the CTAF. So, you can get a clearance on the ground there despite the lack of direct radio contact with ATC. The accident airplane was filed and squawking a code.
A C185, N185PG, flew over Watertown at 4,000 feet about 5 minutes before the accident. They're probably the ones who have the best idea what the conditions were there!
Registered aircraft owner appears to not have an instrument rating. There is another pilot who lives at the same physical address with nearly the same name (probably his son) that does have an instrument rating. Not sure if either were involved in the crash.
After further digging: Registered owner (middle initial A) is the father and has the instrument rating. The other one (middle initial J) is the son and does not have the IR. It's very easy to confuse them because it appears that they are both dentists and work(ed) at the same practice - Dad founded it in 1975, Son joined in 2013 fresh out of Marquette dental school (which was Dad's alma mater as well), Dad appears to have retired in 2016.