Budget these carefully into your overall project plan to avoid surprises.Rehab Budget: Ensure that bids are received from multiple contractors and that adequate reserves are made for cost overruns.ARV: Be conservative on your ARV since the appraisal concerns one person’s opinion.

I've spoken to lenders who don't seem to have an issue with it, as long as the DSCR is adequate.

Quote from @Paul Azad: Quote from @Geri Randall: BUYER BEWARE: Goodegg distributions "paused"Goodegg has stopped distributions on the offering I bought a couple of years ago, called Congaree Villas, and has not been forthcoming with revised financial projections that explain why it has done so--even though it says the property is still cash flow positive and has adequate reserves.

By house hacking, you're immediately positioned as a landlord, which will adequately pressure you to learn how to structure your leases, screen applications, collect rental payments, resolve the nuances of managing tenants and addressing property issues, etc.

If OP can lever-up while maintaining adequate reserves, he will be in better position than buying with heavy cash position.  

The owner should look at it more like a DSCR, and should be pricing the property and offering terms such that the income from the property is adequate to pay back the loan.

You will want to consult with a lawyer.In regards to your last two questions here's some background on what makes a contract valid and enforceable:Offer: A promise to do or not do something within a certain time period Acceptance: A clear and direct statement that all terms and responsibilities are accepted Consideration: A legal and adequate inducement given in exchange for the promise Capacity: The parties to the contract must have the legal capacity and competency to contract Awareness: A party must be aware of the contract Legality: The contract must be legal in the jurisdiction it will be operating in***Not legal advice*** Steps I would take: -Review contract in detail to understand each counterparties responsibilities (if you are not aware)- Email a copy of the lease to each of the tenants listed on the lease and reiterate lease expectations for termination notice, rent payment etc. - If the lease was signed via Docusign (other esign may have same ability) - you can go to the envelope, go to history and view the IP addresses for each action taken.

VRBO bookings in that 30-day window, I would then go live with my Airbnb listing, open out the calendar a little bit further so adequate availability shows, and take advantage of it’s first week or two?

For a few rentals, forget the LLC's, just get adequate insurance. 

In Chicago you request a CHA Burden sheet and that gross number minus utility allowance will be what you get in addition to making sure bedroom size is adequate.