Scruffy depreciation recapture is an important variable that would help to analyze your situation in a more efficient manner. How long have you owned each property, what is your original basis, and how much have you depreciated out is important.
To be honest I would not even begin to try to answer your question without a more comprehensive look at your overall portfolio. Do you have any other capital gains losses you are carrying from other investments, etc…
Do not, I repeat do not try to answer this question as you have posed it… this is a question that you need to sit down with a financial planner and analyze.
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One thing not mentioned but unfortunately they are now highly regulated are private annuity trusts. These are pretty nice instruments for highly depreciated assets. However, the IRS now provides a high level of scrutiny for these instruments. If utilized properly they can save you a ton of money in deferred tax savings while providing a robust income stream.
Anyways, I believe there are other factors you may have to consider and should work with your financial planner to do so in order to come out with an ideal solution. So I mentioned the PAT because it was an option you did not mention.
