Though, even through house hacking, not having any capital cushioning me in the event I have a room(s) go vacant for too long makes me extremely uncomfortable, and I'd rather just wait until I'm able to invest without so much risk rather than getting in over my head and setting myself back with even MORE debt.     

Ultimately, it is a business and gwtting to close could lead to uncomfortable situations.

I’m a pilot and I like checklists, systems and routines to automate my processes.

I feel as though as a lender, I am giving this guy my referral even though it’s through my wife and it makes me feel some what uncomfortable.

It can be an uncomfortable conversation, but a necessary one.Whatever you all decide is fair, then get this down in writing and drawn up by an attorney.

Ladies, similar scenario - male tenant makes you feel uncomfortable etc, what steps do you take?

There are advantages to the owner doing this such as routine cleaning of the property and guaranteed rent to be paid on time, fix any repairs etc.This would allow you to take that $50k and and get multiple STRs as opposed to only one.

But having some of these uncomfortable conversations ahead of time make for a much smoother operation and partnership through the life of the deal.My partnerships are done in LLCs with operating agreements that spell out EVERYTHING.

The female who sent me these has know said she feels uncomfortable living with him now.

What I gathered from the call: They will provide comps of the properties in the neighborhood to support the purchase price, they check in monthly, and return earnest money if in anyway you are uncomfortable with the appraisal coming in low.