I am currently inclined to buy another one as the HELOC interest is 100% tax deductible hence I may keep it as a "never ending" nor growing debt.

Just think about your insurance deductibles for those bigger claims like hail storm. 

When looking at real estate all assets classified as 15 year land improvements and 5 or 7 year personal property qualify for 100% bonus depreciation, meaning you can deduct their entire cost in year 1 instead of spreading that deduction out over 5, 7 or 15 years.

Regarding Condo Exterior repairs, it is also common for a major repair to require additional funds over the HOA dues, so a Special Assessment is often levied.   

I'm curious as to how tax deductions work in this situation?

At this point I want to have initial meeting and see where the insurance companines are with their offers to settle (I also had about 70% of policies with one carrier) but every parcel is a seperate claim, deductible, adjuster, process, etc.

Your kid might have to file a return if he is not right now 2) Your rental loss might be lost as your son will have no basis or at risk amount in the partnership to deduct the rental loss.

I deducted from his deposit for the month of August, but still hasn't paid for September and keeps saying that we'll work it out.

Rent is due in advance and in full on or before the 1st day of each month without deduction or set off.

We paid $30K, and the new one will be in the area of $60-65K.Are we entitled to deduct any depreciation or capital losses on our income taxes?