Hi guys!So I'm a resident physician living in the Bay Area and my fiance owns a 3 BR 2 BA condo in the North Kenwood area in Chicago, a 6 unit multifamily condo building. The HOA was severely mismanaged by a self-mana...

The job situation is complicated.

A legal entity such as a LLC is for asset protection, not tax benefits unless you are investing with a non-spousal partner.If anything, forming a LLC will make it more complicated and expensive.That’s the short of it.

But for some reason even the house hacking posts contains a lot of calculation of CF, Cash on Cash Returns etc - sound like a lot more complicated than my experience with the condo and what I am imagining? 

Too complicated of a structure defeats both of those goals.

You know I firmly believe Pittsburgh is the most complicated city to understand in the Rust Belt, so if it works here, it works anywhere. 

Our attorney suggested that we get a Vacancy Affidavit, which we can then use to shorten the post judgment redemption period.Instead of having to wait 90 days to go to judicial sale (after the judgment hearing), it will be more like 30.A big bank probably wouldn't have caught that or even cared that they could shorten their timeline.

I had always planned to do it all myself to minimize complications but stumbled across an opportunity to partner with someone on syndicating a large multifamily property and I’ve been hooked ever since.

And being in Hawaii for tax benefits they do semi complicated Solar projects there in the islands  

Here's a couple sources where you can read more on this if you're interested:Connecticut Office of Legislative Research: Late Rent Grace Period and FeesState of Connecticut Judicial Branch Superior Court: Rights and Responsibilities of Landlords and Tenants in ConnecticutRegardless though, in my experience, while us landlords may generally focus on due dates, most tenants focus on a different date.