Hold periods need to be adjusted.  

If you can get the adjustment you need to cover all or most of the structural damage, the numbers start shaking out better. 

Thats aside from guest management, daily price adjustment and all the remote work.

Adjust the lease term prior to closing, period.

Apply, move forward, fail, review, adjust, retry, succeed, create new goals & repeat.

I personally made some adjustments but overall it works well to analyze deals. - The weekly calls are consistent and offer great support to getting deals locked up. 

I moved form Arkansas and am still adjusting to the cost of living here.

If something sits for longer than 2 weeks in prime leasing season you should consider adjusting price, marketing package, or easy to change amenities (appliances, include window AC, dishwasher, etc. you really need to review competing rentals and see what they include).

I understand the adjustments and concerns.

The second property will be purchased with a mortgage (you can determine how high or low the leverage will be by adjusting the proceeds you use or the price point of the 2nd replacement).You are adding some measured debt at a level that your dad can be comfortable with.