My partner however is NOT a real estate professional and won’t be able to capitalize on the deductions as much as I will be able to due to their share of the “loss” being a passive loss.

Im sure there are worse properties out there to start with.

Even if it is just a walkaround and not measuring anything; the contractor should be there if you are new to this to give you an estimate.. 

Expected Nightly Rate: What’s the best way to estimate this without over- or underestimating? 

The reasons they identified will not impress the judge and you will win as long as you followed the proper procedures.There is no way to ensure that they won't damage the property, but you have recourse if they do.

@Rene Hosman will be able to help you figure this out.

Let me know if I can be of assistance. 

Using a HELOC can work, but it's still a second loan on one property so I wouldn't be looking for a way to leverage one of your two properties just yet to get a third.

I am new to the real estate world.

If we are analyzing a turnkey property, is it reasonable to decrease the repairs and capex to like 5% each?