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

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.

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

We were thinking about taking a loan from that to put a down payment on investment real estate, but he said that he thought he wasn't eligible because he was no longer technically employed.

My quick research indicates that while there is legal precedent (albeit from 2000) that this would be technically treated as a sale, only the principal and interest paid via seller financing amortization schedule would be taxable.

The IRS audit techniques guide is an easier and more practical reading, however still pretty technical and heavy.Finally, one important point that you may not realize: even if you do qualify as a REPro for 2018, only 2018 expenses will be unrestricted.

We don't technically offer substantial services, so I think we'd take a risk by doing Sch C for the refund this year, especially if we end up switching to Sch E down the road.

I was more about how using Wordpress allows a regular person to build their STR booking site without a ton of technical knowledge.