We bought a house and paid cash for it, forced some value into by adding over 1800 square feet onto it with very little cost due to an addition that was already started prior, and updated the house built in the 80's.

In your situation, I would charge for the prior fixture in some form (but would not want to be in this situation).

However, ensure that your decision does not violate any anti-discrimination laws or local ordinances.Make sure that:The records are accurate and pertain to the applicant.You have established written criteria for tenant screening, which should include reasons for denial such as prior evictions, judgments, or debt-related issues.

Is it better to use "involuntary conversion provisions to take a deferral of the gain on the loss of the previous roof assets and continuing depreciating the prior assets as is"?

As a landlord, I verified the work needed by pictures being sent, and arranged for a contractor to go in person who is licensed and insured to give an estimate for the work stating to management company this would likely have to come out of a security deposit.The management company was initially asked prior to me arranging this appointment with contractor, to have someone professional quote the damage, and they disregarded my wishes and without my knowledge, or notifying me, granted consent to the tenant to fix the door " in any way they see fit, and to attempt to fix it themselves to the degree of their liking." 

As far as I can tell this tenant has a handshake agreement at this point with the landlord prior to me. 

Well, if you are truly working on a cash flow statement, you can't really record the cash flow in a time period prior to when it was received. 

I intend on doing a cosmetic remodel prior to selling down the road but it's not ready for that.

And as my target tenants are traveling and may not always have access to a larger computer screen that is something I will look into prior to the next tenant.Good luck, and thank you so much for the information.

@Chris Seveney this is a sentence is an NDA they (broker) wants me to sign prior to receiving property info.How would either of you progress with this in getting property info?