If you can give a bit more info about the property, you can get more focused recommendations.

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

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

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).

@Jacob HavlovickBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

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

If house hacking isn't the best option for me, how would you recommend starting out to build up some investments.

I'd love to hear what other people are doing and recommend; tips and tricks for guarding a vacant property. 

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

We would never recommend that for our clients.