@Brett RiemensniderYou don't need to provide anything to your tenants tax-wise.

Also note that my company will possibly either cover closing costs if we sell or provide property management for two years if we rent.

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

Yes, an investor agent, an experienced rehab contractor and a very experienced private HML that is also an investor, all of which provided invaluable guidance.

They provide fake checklists saying units are repaired according to agreed-upon inspection reports only to walk in to a home that is more damaged than it was during escrow.

Liability Protection: Transferring to an LLC provides asset protection but may not always be worth the hassle or cost.Next Steps: Review your loan agreements, consult your lender, and get advice from a real estate attorney and tax pro to ensure everything’s compliant and beneficial.

They might be interested in partnering or providing funding for your project. 

If it's currently an STR they should be able to provide you with the p/l statement from prior years so you can see gross rents, operating expenses, average daily rates and occupancy levels.

Can you provide guidance on how to get started and some effective strategies?

Would the info you provided still be the same?