@Jonathan B.Assuming you pass the "material participation" test for 2023 and did not use the property yourself (or used very little), you should be able to treat it as an STR for 2023, including bonus depreciation.  

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?

As for the rest of it, you can find a lot of useful tips on past forum posts along with podcasts and youtube material on the topic (BP and other RE sources).We've self managed STRs for a few years.

That will increase your material costs for the job and is the contractor paying for the material in their bid or are you paying for it and paying them a labor cost.

The house's exterior is constructed of brick material with a flat tile roof.

I put together an investor package that has info on Cleveland markets and different strategies.

Choosing pre-selected materials can simplify the process.- Managing Multiple Projects Simultaneously: Handling numerous properties at different renovation stages requires effective project tracking, milestone-based contractor payments, and solid contingency plans to navigate potential delays.- Technology & Automation: Utilizing project management software, such as Buildertrend or Monday.com, enables real-time tracking of budgets, schedules, and contractor communications.

Your roof and exterior material?

If you continue using it as a rental but reduce STR activity below the material participation threshold, your deductions may become passive and subject to loss limitations.2.

Line Item Fee Collected Rents 10% of All Collected Rents New Tenant Search & Onboarding $500 Business Hour Service Calls $80/hour + Materials Cost + Tax After Hour Service Calls $110/hour + Materials Cost + Tax HVAC Cleaning & InspectionGutter CleaningSpring/Fall Exterior CleanupSeasonal Mowing & Weed TrimmingSeasonal Snow PlowingGeneral Contractor Vendor Cost + 10% Oversight Fee