My concern is if I start renovations now, the life cycle replacement on these items starts ticking once they’re installed vs if I wait a little longer.

If using Schedule E do they add back in PITI+Depreciation since PITI is already counted in Debt itemization?

They carry some different items like window cleaner etc that I also buy there.

That will be a long list of 1000's of items to track over the next several years at tax time.  

I use Honeywell 9000 wifi thermostats that send me alerts for humidity or temperature levels I configure.None of these items have monitoring or monthly fees.

@Christopher Fordinal  Good point, I need to add an FFE line item in there, thanks for pointing that out as I usually just include in the rehab total.  

Connecticut tenant/landlord law governing security deposits leaves it so vague, just saying you need to provide an itemized list with amounts “of repaired damages, not including normal wear and tear”In my eyes, he signed the lease saying no smoking, the smoke smell wasn’t there to begin with, and in order to remediate it back to move in condition I have to incur a charge to get the proper equipment.

The necessary item is that you need to occupy the property. 

In a vacuum, if the interest rate on the student debt is higher, you should pay that off.That said, here are items you should consider:- How long will it take you to save up money from other income sources to make another purchase if you were to pay off the student loan? 

Financing statements are used because these items are personal property, not realty.