I work with a lot of high earners and have a few friends of friends that are doctors and lawyers.

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.

. ;-)Some things come to mind-do you host yourself, have a property manager or co-host, is your STVR dog friendly, do you have king beds, where is your market, do you have professional photos etc.

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.

After a year or two we intend to buy a larger property in the same area and partner with some friends on it but I do believe a boots on the ground person employed only by you is KEY to executing anything if you are not in the country yourself.

These people can be relatives, friends, coworkers, friends of friends, and business associates.

I'm SURE you mis-spoke and meant to say, he's a close friend that I am trying to help but it was not my intention to "fix his credit".Debt Relief and Credit Repair Scams"The FTC has brought scores of law enforcement actions against these bogus credit-related services, and the agency has partnered with the states to bring hundreds of additional lawsuits"SOME CASEShttps://www.ftc.gov/news-events/topics/consumer-finance/debt...Financial Education Services (August 5, 2024 )Panda Benefit Services, LLC., FTC v.

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

Definitely connect with an investor-friendly agent, they should have all the knowledge, resources, and connections you will need.

and even for friends and family, that's more of a favor than a loan...you asked not to sugarcoat, so here goes.