His advice would lead you to 7 years of skipping a hugely beneficial deduction and still incurring tax when you sold as though you DID get that deduction.

Otherwise I would lose out on mortgage interest deductions on taxes, and could owe taxes I pay my LLC in rent, right?

or are you just deducting your mortgage from your prospective rents?

This strategy makes sense especially if you used to itemize but now are taking the standard deduction since it was increased so much.Fidelity has a good charitable gift trust that is easy to use.You could also look at increasing your 401(k) and HSA contributions this year.

Can i deduct all my expenses for this property on schedule E for example and use the loss to reduce my taxable income? 

Use them as your deductions. 

You can also deduct any expenses related to the business. 

I don’t like the wholesaling strategy because I feel it’s very short sited when you start to factor in the tax deductions / appreciation of a property vs the tax your going to pay on your quick sale cash return.

I believe if AGI is $100,000 or less, $25,000 in rental property can be deducted. 

Tax advantages like losses and other deductions are what interest me.