Rental Income / Expenses Proration and Residency

I own in a house in Florida that I lived in for 6 years before recently deciding to rent it out and move to Wisconsin.  I posted the house for rent beginning of September 2023 and stayed in the property to fix it while it was trying to rent it.  I rented my property in Florida starting on October 6th, 2024 and also claimed residency in Wisconsin on this date via change of address.   I received first / last months (2 months) rent on September 29th, 2023.  For 2023, a total of 4 months rent was paid. 

 

1.) Can I claim any expenses / deductions for September 2023 while I was fixing my property for rent? Updates that I did in 2023 and prior years?  E.g. - Impact Windows / Doors

2.)  Given that I began renting my property October 6th, 2023, do I prorate the rent received for October 2023?  Prorate Expenses?

3.)  Do I need to report the 2 months rent received on September 29th, 2023 as Wisconsin income given I was not a resident until October 6th, 2023?

4.)  Do I prorate 2023 expenses or use full amount on the date/year I paid?

  • E.g. - Water Bill paid date - 01/17/2024, usage for 12/15/2023 - 01/17/2024. 
  • E.g. - Internet paid date - 12/15/2024, usage for 12/16/2023 - 01/15/2023
  • I am assuming these expenses are prorated per day?  Mortgage Interest, HOA, Property Insurance, Property Taxes