Does anyone have recommendations for a contractor for an almost full gut property in Rochester NY?

I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

3.Any recommendations for contractors or permit expediters in Covington who can assist with this process?

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

For financing, I recommend you reach out to @Andrew Postell

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Platforms like Procore, JobTread, Buildertrend, and FlipperForce have caught my eye, but I want to make sure I’m considering the best fit for my needs.Here’s what I’m looking for in a solution:Cost Estimation: A tool that accurately calculates material and labor costs.Project Oversight: Features to manage tasks, schedules, and budgets efficiently from start to finish.Vendor Integration: Real-time updates on pricing and inventory from suppliers like Home Depot or other suppliers.Material Suggestions: Automation or recommendations based on the rehab’s scope and specifications.Labor Planning: Tools to predict labor hours and staffing requirements for each phase of the project.For those of you who’ve used any of these platforms (or others), I’d love to hear your thoughts:Which software have you found most effective and why?

If the home has a really nice layout or beautiful interior and it's not getting many showings, I would definitely recommend a video tour.

I recommend you go to the source and educate yourself on all the landlord-tenant laws, particularly in an increasingly regulated state like Colorado.Here's a good starting point: https://doh.colorado.gov/landlord-rights-and-responsibilitie...

I cannot recommend RTR enough, they are the best!!