I've had a full time individual working for me for almost 3 years and she handles almost all of these items.

@Jesse Jones-Smithhi. i tend not to advise people on personal residence items because... it's too personal. so i'll just pick one thing you mentioned and provide a comment. 

I'll preface by saying I'm not a tax expert, but just went through a cost segregation as a REPS and this was my view.The benefit from pulling out these items coupled with the bonus depreciation far outweighs any incrementally higher taxes in later years, by quite a large margin. 

After analyzing our reviews with Chat GPT (something we should all be doing), we found this was the most commonly mentioned item in our 5-star reviews.

Generally people might budget 15% of incoming rent for these items.

Having rental property is not what determines if you are going to take standard deduction or itemized deduction.

Your attorney should be able to help with this as they will likely want to get an itemized list of projected past expenses.3.

What construction items should I be in the lookout for due to hurricanes?

This is bogus if buyer and seller are independent parties (if the parties are associated then I understand setting true value) as there is usually a reason for the discount purchase (risk items like unpermitted work, crazy low rents in rent controlled area, hoarder, heavy need of rehab, etc).  

Laws are ALWAYS evolving and every couple years there is likely one or more items that should be updated in a lease. 3.