Already have a STR in Frisco, CO and Summit County is a real pain in the tail for owners of STR.

It gets painful to see deal after deal go to someone else, but I wouldn't want to be owning the assets they bought, at the price they bought, if the market downshifts significantly.

Your ONLY remedy is money...how much it will cost them, at some point, and usually after more pain in terms of posting/mailing notices, going to court, etc.Will the cost to them for not moving on time be greater than the cost to you for not being able to provide someone with your signature on an agreement the premises you promised?

If you simply bring value by identifying their pain points and offering actionable solutions, all that follows will be simple including gaining their trust, business, or sale. 

It can be a pain to deal with them.

. - It’s a complete PAIN. - Make a list of all banks and account numbers, all investment institutions with account numbers, lists of credit cards, utility accounts, etc.

Redundant and a pain. 

I'd definitely go with a 5% down house hack - no questions asked.I feel your pain not wanting to live in through a flip as well, been there and won't do that again either.

., sometimes only a change in type location or demographics will get rid of the pain. 

Secondly, I trusted my realtor too much and didn't verify all the information about the neighborhood, expenses, vacancy rates, etcThird, I assumed that rents would go up.Now, after owning the place for 6 months, I find a lot of pain points1.