I have a lender, I would work with the same law office as previously, I have an insurance agent, I would find a home inspector, I would coordinate with the lender on the assessment - I feel quite capable of managing all of that. 

With regard to the contractor, you want to give proper notice for when the contractor will come to do work and that depends on your state's laws and also your lease.If you give proper notice and the tenant refuses entry, then I would talk to the tenant and explain to them that they are violating the lease and could be evicted if this continues.

Like other cities Indy doesn't have progressive zoning and permitting laws.

If you're looking in DSM, we use Aaron Hubbard at Hubbard Law.

The permitting and law does allow a home owner to do the work, and then inspected (which are more thoroughly done) if they live there themselves for a minimum one year.  

You don't know the law, you don't know how to handle difficult tenants, and you aren't local to work on it.This is what Ohio law says: “The tenant shall not unreasonably withhold consent for the landlord to enter into the dwelling unit in order to inspect the premises, make ordinary, necessary, or agreed repairs, decorations, alterations, or improvements, deliver parcels that are too large for the tenant’s mail facilities, supply necessary or agreed services, or exhibit the dwelling unit to prospective or actual purchasers, mortgagees, tenants, workmen, or contractors.”I would give the tenant a short, direct warning that they have 72 hours to coordinate with the vendor and set a schedule for repairs.

I would recommend you speak with your tax advisor and set it up correctly from the start, whether an LLC, Trust or something else.Also consider states different laws, maybe find a state with more friendly landlord protections. 

In 2024, my neighbor replaced the back part of the side fence (He paid for it 100% and didn't give me proper notice per CA Good Neighbor Law).

Their in-laws just had a house built as well - it was completed back in June.

However, I had insurance coverage that I was advised was appropriate and I operated by what I understood landlord/tenant law was and used professionals.