Since it is a sub-to deal should I use Turbo Tax, a general CPA, or a CPA specialized din sub-to?

I'm looking for referrals for a custodian, tax attorney, and a CPA to set one up and advise me.

I am unaware of any law in any state that requires you to have a CPA.

Absolutely recommend going with a CPA (a little biased) that works in real estate.

If real estate is involved, separating it into its own LLC before the sale can simplify the process and make it easier to leverage a 1031 exchange.This post does not create a CPA-Client relationship.

We just switched over to a CPA for our taxes after getting our 6th investment property.

Consider balancing liability protection with administrative costs, and consult with a CPA to align your structure with your financial and legal goals.This post does not create a CPA-Client relationship.

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).

Financing might be a challenge.I would recommend consulting with a attorney, loan officer, and CPA to discuss your specific situation and determine the best course of action. 

Electing disregarded entity status avoids additional filings while achieving the same tax outcome.This post does not create a CPA-Client relationship.