I am a big fan of the less gentrified neighborhoods of Hermosa, Little Village, Uptown, etc. in addition to the Opportunity Zones with regards to capital gains tax deferrals.

Would you ever consider purchasing a house hack that has a small amount of negative cash flow (when considering all expenses to budget for, of course), knowing that cash flow would be positive once you moved out and gained income from the unit that you were occupying?

There’s also the huge benefit of using an FHA loan, but I’m not sure I would be able to sublet my apartment here in the city to occupy the property for the first year.Then, I think about the pros of having the tenants next door: they are next door.

Also, I sought to obtain a property with a good chance of gaining some equity in the coming years.

I offer the option to pay 3 months of mortgage as long I hold the right/benefits to sell the house.

Hoping to gain some insight on a potential rental I’m trying to purchase.  

Another potential issue is how to most efficiently structure the LLCs to gain financing, though this is likely offset through personal guarantees, which we are willing to do. 

The law is complex and depending on your income level may provide you with absolutely no benefit.

Even your Bank may not allow a 2nd note see the contract and see if it contains any language about that.Remember that the bank does most things that will benefit them, not you. 

I work pretty closely with an insurance group now, but I would still be happy to connect to see how we can benefit each other down the road!