I have a couple questions since I am just starting out, and I am often experiencing some of the things you mentioned.

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

Quote from @Mitch Holmes: I would flip as well, as Chris mentioned.

Not to mention they have a dozen other agents just like you busting their tail for them. 

As you mentioned, you can take losses from stocks, but your capital losses can only exceed your capital gains by $3,000.

The person who gave me a demonstration mentioned that by using it, listings were much better ranked on Airbnb (he emphasized that the listing updates every night, which is good for the algorithm).

BTW, in your example since you didn't mention having signs up about the sealcoat (the one very pertinent detail), then of course your office would likely be liable to pay for their shoes.

Quote from @Lee Mobley: In Georgia, there has been a default judgement entered against both Outstanding Real Estate Solutions, Inc. and Chimene Van Gundy for $200,104.53 plus costs as well and a default judgement entered against Michael Trofimoff and Viridis Holdings, LLC total sum $197,334.45 plus costs for similar issues mentioned in other comments here. 

^^ not a way to get around the net income for your rental, but as mentioned DTI restrictions are different from lender to lender so you might find more leeway looking into that. 

.: @Jonathan ChanYour other post mentioned about your mom's SIDRA doing lending.