For background info:*I have a trust that owns a holdings LLC, and that holdings LLC owns my operating LLC.

Technically, if that is the case, I wouldn’t be profitable until several years down the line.  

I have 1 STR (technically 2 on one property) and am looking to purchase my second property.

There are both pros and cons.Do NOT try to read Section 469 of the IRS code, unless you have tax/legal background.

(BUT when qualifying the tenant's income, they only need to qualify for their portion). 2) Consult an attorneyyyyyyyyy :)3) Standard I've always used is no more than 7 days per month and max of 14 days per year, otherwise they would be considered an Occupant and need to complete a background check and add to the lease. 

When there is no buyer's agent, the seller's agent keeps the full commission amount as they technically become your agent as well and will represent both sides in the transaction. 

As Bill said, you'd technically need to remit market interest of ~5-6% to avoid a related party transaction, but since $100-120 would be vastly below their annual exclusion amount, you can just say that any interest that would otherwise normally accrue would be considered a gift to you.

For sure you would "technically" need to pull permits for something like that...but this is likely a case where doing that work isn't going to alarm any neighbors or city officials...Being that it's inside your unit and an enclosed porch.Sam is great and so is @Prashanth Mahakali as far as local Chicago architects go.

I can also share the source we use for background checks.

Hey Alan, Technically this would not be considered an investment since you have a relationship with the tenants.