We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

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

It also depends on how you hold your properties; LLC, S Corp etc... as to what the agent will recommend.

It's pretty common practice to have something like that in a property management agreement, and if it falls under that limit they're going to pay it and not notify the owner except in regular monthly updates because it is below the threshold of what is an ordinary expense in the course of business.

Anyone with experience that can recommend a path forward?

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

As long as you follow the two-year holding rule and structure the deal properly, you should be able to move forward, but I’d highly recommend working with a tax pro to ensure compliance.Disclaimer: I’m a licensed real estate broker associate in Florida, not a CPA or tax attorney.

Going live as a STR in 2 weeks Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Also if you have any areas you recommend and why I appreciate that.

-------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?