Hey @Mitul Gandhi - Generally speaking, the neighborhoods in Chicago that have the least taxes are going to be the neighborhoods that have the lowest property values.Properties that have been renovated (and a permit pulled) will typically go up in taxes because the city knows that there were improvements made.

I know that’s not the typical response for an investor, but I do things a little out of the box, and it has provided me well so far.

However, it's also true that financing options can be more limited for LLCs, especially when it's a new entity.One alternative worth considering is forming a partnership agreement between you and your friend.

This will bring cash reserves to over $200k which is more than we typically keep. 

I have personally been involved in house hacking and furnished rentals for over five years, and it's been fascinating to see the quality of mid-term tenants we've had over the years.However, it's worth noting that in our area, the demand for short-term rentals on platforms like Airbnb and VRBO has declined in the past 24 months.

I don't know if they cover your area, but maybe its worth a shot?

Though, it's worth looking into. 

Nothing worth putting the life jacket on...

As much as I am looking forward to getting away from Quickbooks, there are a few pros worth mentioning.

Here's the difference between the two - a CPA typically has to have a bachelor's degree in accounting and masters level of education then pass a series of difficult accounting exams, while an accountant may have zero qualifications; this could be your local bookkeeper who learned everything on the job.There is also an Enrolled Agent.