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Well damn, clearly I need better guidance on tax planning... what are some ways to tap into those losses aside from selling?

Arbitrage has been discussed ad nauseam for the past 5+ years, and the overwhelming consensus is that you should avoid it.

Tax Benefits: Florida has no state income tax, making it an attractive location for investors seeking to minimize tax burdens.5.

I'm currently living down here but all my financials (assets, bank accounts, income, tax filings, etc) are in the US.

But you can still treat it as resulting in Ordinary Income even though it is reported on Schedule E, which lets you properly report in accordance with the tax results it seems you are shooting for under the tax return loophole.If your CPA is looking at switching it between schedules to get that tax result...it sounds like they don't understand the reporting position fully and/or they just don't know how to use their own software to address it.In summary, based on what you are describing for the situation, it should go on Schedule E, with what sounds like the resulting refund of $17k.

I also look at capital appreciation, tax savings, cash flow and cash flow appreciation.Where you invest, investment support structure for each property, and additional factors important to your individual decisions all make a difference as well. 

If I use reward points for the flight/hotel/rental car, am I able to apply the value of those points to my taxes for the travel?

Still need to get my taxes done this year for them.

I want to be fair.The lesson here is avoiding the temptation to grab those checks and cash them.