We ran it past our real estate agent and lender — but I'm all for shoring up.

Contact the real estate division for confirmation: https://idfpr.illinois.gov/dre.html 

Thank you Jay 👋 Do you invest in real estate as well as act as an agent?

I wouldn't own so much real estate if I didn't make RE my primary business.

To be considered an investor (and possibly get long-term capital gains rates), you’d need to hold the property for over a year as a rental or investment, not actively flip it.Check out the IRS guide on rental real estate and capital gains for more details: IRS Rental Property Tax Guide.You might want to talk to a CPA who specializes in real estate to see if there are any strategies that work for your situation.Good luck on your flip!

I am kind of new to real estate investing as I got lucky the first two times but now I am looking to invest quite a bit more money and I am slightly terrified. 

Based on what my real estate agent thinks that this quote will be, roughly, and the after repair value, it looks like I could buy this property in cash, spend a month or two fixing the damage, and then put a mortgage for roughly 1.6x what I paid for it and thus have a cash flowing property at a few hundred dollars per month and a little more money in my bank account ready for a down payment on the next deal.

I'm a real estate investor in other parts of the country but not NY due to the extremely high buy in price.

.: Its typical for real estate investors to hire a private home/building inspectors to inspect a real estate property before they buy it.

Things like the real hardwood floors, claw foot bathtub, and stylish kitchen.