Like with any rental, tenant screening is crucial in this area because opioids and other drugs have hit the area hard. 2019 has been my first year without an eviction so it has been a learning process.

When the wind hits 30+ the waves will hit 3-5ft.

I’ll probably take a bit of a tax hit in order to 1031 without carrying the mortgage across.

We do put them in collections which hits all 3 credit bureaus and doesn't cost us anything. 1.

On the next steps you have hit a lot of peoples dreams.

I had an alert sent from Zillow when this house hit the market.

I bet you are more like 3-4%. 3) Would you take a significant capital gain hit if you sold? 

What options do we have for locking in purchase of the property NOW & him avoiding the tax hit of an immediate sale before it goes back on market next year.

You could have a few things driving the cost:-Location - if the house is more remote the contractor will have higher costs to get out there (gas, lodging, limited resources) or if you are using a local guy he might be higher because he knows there are fewer competitors -El Nino - the roofers we use are all busy because people are rushing to get work done before the rains hit.  

If the seller's price is unrealistic at first, its OK because you still have leverage... the property won't hit the market until Fall AND you know more about this property than anyone else.