Are there any strategies I could use to still claim the depreciation, or any way that the transaction could be structured such that I don't lose on that tax benefit?

New supply and rising expenses are probably even more impactful.Florida has some of the most new construction going on in the country, and is seeing rapid increases in insurance costs.

All of my properties (8) are between 50-100 years old and I’m confident are worth much more than a new structure in a cheaply built community.

On the other hand, if you find a supply vs demand imbalance in a cheaper market, prices and rents can rise unhindered. 

I feel like at this point we would do well to talk to a partnership lawyer that can help us dig through options and help structure.

Let me know if you’d like help analyzing the financing options or structuring the deal!

If you demonstrate a good track record, securing future funding becomes easier.If you're considering this route, structuring your deals with private lenders could help you secure financing quickly and move forward with more projects.

Best for short-term use, as rates are higher.Given your strong W2 income, excellent credit, and LLC structure, any of these should be feasible.

It’s why structures adjacent to vacant parcels due to demolition historically trade at significant discounts (not only because of the issue you’re grappling with but also the risks associated with underpinning and the construction process if and when the adjacent properties are redeveloped).

As for a generational lineage plan, it's best to assume at a future date you will liquidate EVERYTHING, roll it into a fund of some type be it in syndications, W.S. or what-not, and than the heirs will "manage the managers" as this is the most realistic long-term multi-gen inheritance structure.