Hi @Deepak Jebar, The sale of your condo would still qualify for the 121 Exclusion (Section 121 of the Internal Revenue Code) since you can say that you lived in it as your primary residence for more than 2 out of the last 5 years.  

For me to be willing to sell something in that fashion I typically require a 10% down payment and charge 7.5%-8% interest on the remaining principal with a 2-3 year term.You don't need an LLC to own the property jointly with someone else, you can simply take title as joint tenants and put some sort of operating agreement together.  

After debating internally, I decided to give on this point and allow them to pay me not using the convenience of Cozy or any other auto-pay method.

He studies the Internal Revenue Code updates 4 hours a day and is genius with staying in the lines of white and extracting all available business tax deductions. 

Principal Financial Group, my former employer, is an international firm with offices all over the country/world.

I prefer the old-fashioned method.

I'm looking to house hack this property and get my feet wet with tenant interaction while managing costs internally to meet the cashflow goals I'm seeing in my models. 

I always check with my tenants & let them know what's going on - usually, they're so glad things are getting fixed "in a timely fashion," they don't care when it happens.

So you can win in either scenario...But you could also have 3 people and their possible internal drama, their vehicles, and guests (also with their vehicles).

I've also interned at a large multifamily development firm and learned the basis of underwriting large commercial multifamily deals.