Hi everyone Looking for a little guidance here to understand if there are any advantages or disadvantages to timing on my scenario. Under contract on a home in Florida to utilize STR loophole. We will need to get our 2 stays in Nov-Dec. The home is currently furnished and running as an STR, but it’s performing poorly with aging furnishings. The plan will be to refresh the house with new furnishings and paint. Also, adding a pool, which would begin in December finish in late February. Question is what are the advantages or disadvantages of timing the refurnishing/light refresh? Need the cost seg this year to offset some W2 income.

Looking for recommendations on working with RE lawyer or paralegal to setup entity structure to manage STR’s in multiple states. Any help is appreciated