One property I’m looking at everything is good, they have reserves, owner occupy ratio is good but the roof is currently being repaired through the insurance company.

This would be a turn key on this end- an established property management team and is already in place, it’s recently renovated (no/very minimal repair costs anticipated) and all but 2 or 3 units are already tenanted for the next year.

Therefore, you can deduct items that are directly related(repairs) to the rental units plus items paid indirectly for the rental units(think real estate taxes, interest, insurance).in addition - it looks like you are looking to use parts of the personal residence as a home office.Just note that, it would be hard to prove that you use 100% of the personal residence as a home office. 

I have told him that he needs to take the dish down and will be responsible for any repair costs.

I work full time in IT and maybe able to assist in that area.

He is correct that if you choose to do so, you should do it with your eyes wide open and know the risks involved.That said and done, I never counsel clients to do things that violate their loan agreement, nor do I ever assist them in doing things that violate their loan agreements.

I have been approaching her for years trying to either manage it for her, help with the needed repairs, etc.. but to no avail.

I'd be coming in to cover some of the repair costs, with about $40k of my own money.

My mentor is assisting me with the acquisitions.

What’s your process of getting your numbers on repair estimates?