Since you’re open to different financing options, here are a few strategies that might help:Hard Money Lenders – These are the go-to for most flippers since they fund deals fast.

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

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.

If not, I would advise researching this strategy.

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

Why would you literally wait until the last minute, when a flat tire or difficulty finding a parking space be the difference between keeping and losing your home?

I also think that investing remotely is something I would do after locking down my local strategy.

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.

One strategy is to pursue properties (in your preferred markets) that have been listed for sale for over 90 days (even longer is better).

That doesn't mean you're left behind it means you'll need a different strategy that than someone you started 1,3,5,10 years ago.