I recently had to replace my HVAC system because it was red-tagged.

I haven't sold yet, I've been analyzing property to get a head start on the 45-day timeline of identifying the potential replacement property (and because I enjoy analyzing property). 

Unfortunately - my current lot for my primary is 1 acre and VERY sloped, and close to a water source (creek), so the county has not even allowed me to permit my downstairs finished basement without an extremely costly renovation to our septic (over $60,000, and that doesn't count demo'ing and replacing our driveway to get to the existing tank and leachfield), and even if I could permit it, it would essentially need to be a treehouse in the redwoods due to the slope (not a bad idea though, I would actually love a livable treehouse on this lot!

Just know that it is a "no days off" kind of business and very mechanical.I would suggest documenting your process via video so that eventually you can bring people on to replace the different hats you will be wearing.Keep in mind of these 5 components of any wholesale business.lead generation, deal sourcing, underwriting, marketing, transaction coordination.

I already have 2 loans on the property with great interest rates that I'm not looking to replace.

Have had to replace a furnace and appliances thus far so I'm in 80K *.25 (20% down plus closing costs) + ~10K so I'll be making profit in year 3-4.

Assuming that's true, I would recommend looking for a replacement property (or properties - you can purchase multiple in the exchange) with value of at least $725K (selling price).  

I am going to see if I can switch to a local Wisconsin insurance that reflects our local risk level in their premiums.Many of the homes in the Pacific Palisades are 3-5 million, but when you look on Google Street View, most are very modest homes from the 1960s (there are some $20m ultra luxury mansions too), so a lot is the land value, the home replacement value on a 1600sqft may be what - 500k at the most?

Pilsen is filling in and replacing buildings north of cermak.  

Just replace and move on. install lights.