The tricky part is that if we hold onto it , we surely will be in the red if we decided to rent it out.

If it were 2007 all over again and you knew you could sell at a record high, and invest your capital into conservative bonds and wait until the market corrected, would you?

Am I underwriting conservatively, accounting for higher interest rates, inflation, and potential market softening?

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.

Welcome to the party!

All interest rates and payment plans are custom made to work for both parties therefor creating a win win scenario.As far as partnering with the banks goes.

I would say the cash flow would go up every year and that would usually be the case but my son will be moving into one unit probably for just the labor to rehab the last unit (collected rent will go down for a year).After that rehab is complete, at market rent I would have about $8k/month cash flow with underwriting that most would consider conservative (for example $1200/month allocated to maintenance/cap ex). 

Lastly, make sure to rework your numbers on the conservative side. 

The Chicago Association of Realtors'® specifically state "When you become a Dual Agent, you owe equal fiduciary duties at that point to both parties in the transaction, and you lose the ability to negotiate for, strategize and advise either one."

.: I would never give the party on the opposite end of the transaction POA over the property, or my social, DOB etc.