I’m from Miami would love to start an Airbnb in Orlando I can not say from personal experience.

In many places, daycare costs, commuting, office clothes, taxes, meal prep, all take up a working person's full income when you switch to going back to the office.

Hey Hey @Veronica Mitchell - The most simple advice is to follow the CTA trainlines.I personally love the South East Corridor of Chicago which has Bronzesville, Kenwood, Washington Park, Hyde Park, Woodlawn, and South Shore.That area will continue to be gentrified because you have the lakefront and CTA trains.Others mentioned NW along the Blue and West along the Pink, Green, and Blue lines.

I also have a personal relationship with my contractor so got a massive price break. 

I personally would recommend it but it isnt the best run 3 day. 

I’m not a “people person” so they handle screening.

A couple strategies that could make sense for a younger person without experience could be a live-in flip or a house hack.

Personally, I wouldn't open up a home that isn't in good repair, from a liability standpoint if nothing else.

Now we are in 2025 and although I still own the trucking company, it has been an inconsistent pit that has technically brought me personally no profit.

So now I have both my personal residence and a leased property as STRs.Even though I live 3 hours away from my leased STR property, I've built a team that assists with managing it, so I don't have to be there all the time.Here are some key things I've learned:Regulations: Research the specific STR regulations in the state and city where you're looking to buy.