But you also have to track your material participation time in your property(s) if you're trying to qualify to use your real estate tax loss to offset your other income. 

By default, the tax loss from the rental can't offset your W-2 income because passive losses can't usually offset non-passive income. 

I now see competitor listings at 60+ DOM, so their extra month vacancy already exceeds losses from lower rent…. and they’ll likely settle with a worse tenant.

Breakeven or even a small loss in the first year is not so bad if you need to offset income...and the investor upside is always in the "hold". 

., stocks or mutual funds) that are operating at a loss, if you liquidate those investments to take a loss, you can use those losses to offset your capital gains.

Two months of vacancy every couple of years translates to a lot of rental loss. 

I rented out the property in mid-Oct 2023- Now I am filing my personal and the S-corp return (had a to file an extension given this situation) with passthrough of passive loss into my personal tax return and my CPA is saying I negated the 1031 requirements by converting it into S-corp, which he recommended being in the loop and advising on every action above.

Either get a strong team in Baltimore to give you better options or a CPAs advice to structure your way out of this as a win.Don't consider this specific experience a loss, but disconnect from this investment as a loss. 

2) Can you use OTHER capital losses (from other projects unrelated to the property being sold) to offset the depreciation recapture on the sold property?

The judge said “I’m very sorry for your loss ma’am, but the law doesn’t give me the right to transfer your problems to your landlord. “ she was out.