I have a friend who has a high end property he is wanting to sell.

How are you managing your properties in that area given that property management company seem to be extremely unreliable and seem to go under quite frequently 

Question for any and all.. we have had trouble finding a real estate investor friendly CPA, one that proactively wants to help us learn and obtain all the tax rewards with real estate. 

If your unit doesn't stand out in other ways considering adding amenities like a hot tub, backyard mini golf course, making your airbnb dog friendly, etc.

Once you find a pitbull friendly policy you will find it excludes animal liability, thereby defeating the purpose of pitbull friendly insurance.

He is also a jerk, so none of his friends or family are willing to help him out.

It’s humbing and frustrating, but it also teaches you those guardrails you’ll want next time.. like thorough screening, a solid lease agreement that sets ground rules upfront, and maybe even setting aside a bit more cushion in reserves.Chicago’s got plenty of investor-friendly pockets.

There are some “hot button” topics on BP which bring out “knee jerk” reactions and sometimes incorrect assumptions from some of us long time and frequent participants.  

I don’t want anything in return—just hoping to network, make new friends, and maybe be of help or value to you in any way.If you're up for grabbing a quick lunch, coffee, or beer (on me!)

To maximize returns, ensure compliance with local regulations, prioritize owning the land, and offer student-friendly amenities.