I have been contemplating forming a sole-proprietor LLC, but would that even do anything?

To answer your question the scenario you are contemplating is highly unlikely as there is no shortage of work right now.Best thing to do is talk to multiple general contractors to find out what the costs are in your area and plan for the costs in the budget.

One of my tenants recently told me that a dark spot appeared to be growing each day during the rain, until they woke up with water leaking onto their bed..As I was contemplating how many days it had been getting wet, I thought I would call/text the rest of my tenants and remind them to notify me immediately if they see any dark spots on the ceiling or water around the windowsills, to avoid having anything leak that could ruin their stuff or bother them with additional work if it gets worse.

Actually, I was predicating this on 30% ROI, which is very achievable and is conservative on leveraged buy and hold investments in this area of the country.And this doesn't even consider the hit taken down the road when you pay taxes on at least some portion of your retirement accounts at ordinary income tax rates (accept for a Roth, but I don't think that is what is being contemplated here).I agree that this would be more appropriate for those under 55.However, if you believe tax rates will be materially higher in the future (most sentient humans think this will be true), paying the taxes now at lower rates will offset at least some of the penalty.

I have been contemplating--if I do decide to convert--to do it in stages to mitigate taxes.

They (DOJ) and the agency are contemplating making the sale of redemption rights legal only after the foreclosure sale.

I have contemplated using a site, homesedo e.g., to gather pre NOD lists.

Have you ever stopped to contemplate that these might just be another tool you can add to your investing tool box?

I am contemplating making it really nice like a cobble stone surface or pavers.I have about 1 mile of road to improve, which might give me some economies of scale.

My top income which I was contemplating deferring is taxed at the marginal rate of 25% this year, and who knows going forward.