To report your rental income and expenses on the schedule E and be eligible for rental losses - that would be a rent at a fair market price - especially consider that you rent to a related person.
Non-for profit rental should not be reported on the schedule E and you are not eligible to use any rental losses resulted by non-for profit rental activity.
Generally same expenses that are deducted on the schedule E - would be reported on the schedule A for non-for profit rental excluding depreciation.
You should not depreciate a property that you rent not-for-profit.
At the same time - you may deduct mortgage interest as for a second home and real estate taxes - also on the schedule A but without 2% floor limitation.
But condo dues, home owner's insurance, repairs, utilities and other expenses should be deducted on the line 23.
Let me know if you need any help.
On the rental property, can I deduct the interest on the mortgage and home owner's insurance on Taxes You Paid and Interest You Paid on Schedule A.
Yes - all are deductible expenses.
Do I even bother to fill out Schedule E if expenses (including mortgage interest and Home owner's insurance) are going to be much greater that rental income.
You do not use schedule E for not-for-profit rental.
If I do need to fill it out, Rental income on Schedule E should be what I rent it for (to my son) or fair market rent (to a stranger)?
To use schedule E - there should be for-profit rental at fair market value.
Allowing your son to pay less than fair market value is considered to be a gift.
What are the type rental expenses that go on line 23 of Schedule A, mortgage interest and home owner's expenses or other miscellaneous expenses related to renting. Can I deduct the condo dues I pay since the rental property is a condo?
Yes - all mentioned are reasonable rental expenses. The only difference with not-for-profit rental - you do not deduct depreciation.