If you are just getting started here in Chicago, house hacking is the ideal situation.

While I can imagine some cities might be against "boarding houses" or enforce their "brothel law" I can't imagine too many cities would be supportive of it. 

I know I will get myself stuck in the analysis paralysis stage so I am hoping that bouncing ideas off this group will help me take the leap.

Detached HousesWhen in doubt, consider the tried-and-true detached single-family house.

@Terrence StarkTypically the contract to buy the new house would specify that the builder/seller would deliver the type of plans you are referencing.

Here are the key details of my situation:Rental Property Details (Note: This was our primary home till 2017):Current Value: $970,000 to $1MPrimary Mortgage Loan Balance: $505,000 (@ 2.6%)Took Home Equity Loan on this house to make down payment for my current primary residence.Home Equity Loan Balance: $123,000Total Loan Balance: $628K (Primary Mortgage + Home Equity Loan)Rental Status: OccupiedPrimary Residence:Purchased in 2022Mortgage Rate: 7.3%Current Loan Balance: $650KMy goal for 2025 is 2 fold: #1.

We bought a new primary house in November and had a rental contract on our old house that started Jan.1 2025. 

Im looking at house hacks in Raleigh or Greensboro.

Ended up calling the Jersey City Division of Housing Preservation and in essence the entire home has to be in good order even if certain parts aren't accessible to guests.

What would you do in my shoes I don’t invest there so take this with a slight grain of salt but I’ve heard multiple stories of basically this exact scenario someone getting offered a big payday for something in Cumberland, rejecting it & always for some reason (house burned down, block got worse, sheetz decided they actually didn’t want someone’s land for a car wash after all) always selling for like 10-20k and regretting not selling.