Is there a way to do this legally that would provide a tax benefit?

I removed popcorn ceilings, painted all walls (inside and out), replaced and changed out light fixtures (inside and outside), furnished the entire home, and created a fun outdoor space (fire pit, grill, picnic area, outdoor games - including wiffle ball!).

I think applying your existing skills and experience is some times one of the easier ways to get involved in the Chicago real estate game!

The same for flips, the learning curve is steep and a simple mistake can set you back or take you out of the game altogether.

I'd make sure the agent you're working with knows the campus and STR game.

Bookkeepers are fairly inexpensive for the value they provide.

However, it's always best to walk the property with an agent who can give a decent guestimate on the repair cost of the house to see if the list price will work before sending out a GC.If your properties are ideal for flips and they are actually priced to sell, they will likely go under contract before you can coordinate all of that so you need to be on your game at all times.If you're working with an agent, they should be able to provide you with a rolodex of inspectors, lenders, and GCs they work with to take the burden off yourself. 

If you're new to this game, try to buy rentals, live in 1 unit and rent out other rooms/ units and manage the house well to just understand how to manage a real estate investment and what costs it takes.

In my opinion the best idea is LTR, self management, and playing the long game.

You may seek advice from lenders and brokers on finding a suitable mentor, most will be able to provide one for you.