Show up prepared, ask thoughtful questions, and take detailed notes.

You just buy as many as you can and then figure it out, there is no way to prepare, you just deal with it.

I work for an investment brokerage that specializes in acquiring and selling great real estate investment opportunities.

House hacking is a fantastic way to start, but preparation is key.

You should have a good idea of every expense you have in your primary home, then add the STR specific:  (These are rough estimate numbers, depending on various factors)STR insurance - a special insurance that covers both the property and your liability, could be $2~4k in areas without natural disasters, could be more than $10k in some other areas.cleaning fee - approx. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

Would this be better to try and go through a local bank or is there good options for private money or other banks that specialize in this?

Seller financing can be a fantastic way to get into a 4+ unit property, especially in a competitive market like Chicago.Have you started reaching out to owners directly or networking with agents who specialize in multifamily properties?

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.

Its always nice to be prepared.

I’d love to connect & discuss my goals further, especially since you specialize in long-term, turn-key properties, which are exactly what I will be focusing on as an investor.I’ll definitely check out the podcast you shared to learn more about turn-key investments.