Hi Robert, your situation sounds exactly like another gentleman I am working with right now and helping with his 1031 strategy and execution.

Essentially, the Finish Schedule is a spreadsheet that contains all of the product links, SKU numbers, quantities needed, and installation locations for every single piece of material that goes into your project.

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Most of this cashflow is because they essentially are lowering their negative allocation to bonds.The mathematically optimal path is to maximize RoE at all times (while remaining solvent obviously).

Our strategy is to buy out of shape properties and rehab them back into shape, so a GC with experience in doing extensive renovations at once would be preferred.

Chicago, with its vibrant neighborhoods and strong rental market, is a prime location for this strategy.

My strategy would then be to lease at least two of the renovated units, increasing occupancy to 90%, which could improve the chances of securing favorable terms for refinancing.I haven't pitched it to the seller yet.

If transferring the property to an LLC, be mindful of the due-on-sale clause, and note that an LLC itself does not offer tax savings unless electing S-Corp status, which is rare for rentals.To maximize tax benefits, consider cost segregation, bonus depreciation, and short-term rental (STR) strategies, which could allow you to offset W-2 income if structured properly.

Risk & Due Diligence – Ensure the deal has strong equity, a solid exit strategy, and an experienced investor before funding.

We believe that you set your strategy early on during acquisition, and as such, were primarily motivated by cash-on-cash returns and the strategy, with all of its pitfalls, did result in very reasonable IRR over the many years we have held.