Beautiful and picturesque, adorable small town, Land is in a preservation zone, but there are ways besides subdivision to make money on land.

Guy,You hit the nail on the HEAD!

I'll say again what I said at the start was talk to your lender and get that nailed down as much as you can- understanding that they can and may change terms before you close.

Sellers Info-Main interest: minimizing capital gains/taxes, preserving estate for his kids-SFH free and clear, no mortgage, purchased 30 years ago for ~$150k-Currently acting as landlord, very likely doesn’t want to continue in this capacity My info:-I want to cash flow the property now -I want to purchase the home now or in the future Property info-No tenant, rent comps $2600-2800-Current comps of $290k-320kI don’t know the sellers full financial picture.

Having resources to get major things repaired same day in order to preserve a stay.

Seems like word would get out, but maybe there are enough smaller vendors looking for work that they're willing to take a chance.I remember back in the day there were issues with banks/lenders wanting us to take on AP for them with all the property preservations. 

You can search another one of my posts to give you a sense of generic rehab and maintenance costs, in the end this is the key variable in your underwriting that needs to get nailed down. 

I did have the rental portion separated on my schedule E, so I think Ashish nailed it with his response.

You should be able to quickly nail down what it would cost in your market. 

Now I have had a few homes where the folks never called us back so I have to assume they did not have any cracks or nail pops..