If we are putting in the contract in before we know the cost of repairs, how frequently do you feel we go back to the negotiating table because we really have no idea what the cost of the repairs will be?

I'd be open to it.Charge higher rent.Upgrade your insurance.Require the tenant to add you to theirs.Use a month to month lease so you can boot them if it isn't working out.I have no experience but I'm pretty sure air BNB has their own insurance to cover a lot of these what ifs.The STR will be cleaned a lot more frequently and get less wear and tear than a normal rental.

More frequent inspections perhaps, raise the late payment fee, make sure your lower quality prospective tenant is better educated, and make sure your rental agreement is bulletproof.

Another idea is to frequent the Q&A websites looking for investment related questions, see if any of those spur some ideas.

I frequently tell peolpe that a membership in our group is just like a gym membership.

Ah, Kingston ... we use to frequent a little restaurant/club owned by Zal Yanovsky (lead guitarist of Lovin' Spoonful) back in the '80s... called Chez Piggy, I believe.  

Course a big part of what you pay for is the experience of the inspector and that they are doing it more frequently.  

ONe of my clients I sold a few apartments to he pays 4%  to management plus the onsite manager gets paid by him as en employee to the property that way she can do tenant placement.In the mid west were most of the rentals of SFR's are located or at least talked about on BP here... you could not survive in the PM business without placement fee and 10%.People move pretty frequently in other parts of the country compared to here were we live.You can incentivize your PM all you want but when you tenants lease is up and they want to move you can't punish the PM for that..Also many PM operations in the mid west half to pay realtors or leasing agents ...

I mentioned previously, but the PM portal does not notify you when any changes/updates are made, so I find myself checking frequently.  

I need to be sure that I have cash on hand to deal with problems as they come up, and the few points of return that I might miss out on in the short term are fairly immaterial.Your question comes up quite frequently actually.