For example, I am a little concerned about some aspects of the business cycle recovery and a potential for a double-dip so I lean toward the safest part of capital stack which is debt (or low-debt equity).

Maybe your perception was different, but I remember the sense we had at Wacker Neuson going through rounds of layoffs, dealers defaulting, order cancelations and no sense when the construction equipment industry would recover, or if there would even be a full recovery - ever.. nobody had ever seen anything like it. 2008 was bad, I think Lehman Brothers collapsed in October, by 2009 we had to assume the equipment industry would never be the same.

I have never done a land trustWe have a living revocable trust that we set upHonestly I should have done it 15 years ago but did it like 6 years ago.I do not see the need for a land trust unless you are a politician, actor or athlete (someone who is famous).I have done business with multiple billionaires (not bragging but trying to make my point) including several that owned professional sports teams - and even they did not use land trusts…

Does Wisconsin have any sort of Guarantee or Recovery fund for licensees?

Certainly we can expect some recovery, but all the free government handouts from COVID sparked a short-lived travel spree that seems to be over. 

It took my family years to financially recover. I

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provides support for the property tax appeals process.Additionally, it can help maximize renovations and improvements.A Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.

In summary, if your goals are still similar to what they were when you bought, the location has potential, better vetting of tenants will avoid evictions, etc. it would make sense to keep the property and see if it can live up to the potential you expected when you bought it.If you think you had false expectations or don't see a probability of recovery, I would also do the renovation and then sell.

Initially, my family and I lived in this house for a couple years before deciding to rent it out, anticipating a market recovery from the 2008-2012ish recession.

If the contract exists it is not a mortgage with has "actionable" steps for recovery.