Vacation property sale--opportunity or pitfalls?

In 2017 I inherited outright a family vacation property in the 'lakes region' of southern Maine. I am the 3rd generation owner. The property consists of 4 lots, two on the water and two 'back lots' on the other side of a 1 lane dirt and gravel road.

The two waterfront lots each have a seasonal use only cabin. The back lots are mostly wooded. Total acreage is a bit over 1 acre, with 275ft of water front. One of the cabins has been mostly a rental for many years. The rental cabin has been used for the entire season for the last 6 years by a single tenant--and it works really well. I've given them a break on the rent in return for maintenance labor.

Anyway, the tenant has offered to buy that cabin, the lot that it's on, and the connected back lot.

Here are some details, and some questions:

1. The deeds are all in good shape after probate was completed in late 2017.
2. Each cabin has it's own septic system, and they are both working fine--and have been regularly serviced for a long time. We were careful, years ago, to make sure the septic tanks are on the platted lots.
3. The cabins DO share a common drilled deep well, installed in 2016. Suggestions on how to deal with the water. Obviously something in writing in either the sale contract or on the deed(s). Including shared financial responsibility if/when there is a problem? Or put in something along the lines of, in addition to the above, 'buyer is required to install their own well within 5 years'?
4. Before a sale decision is made, I do want to include our adult children (30's and 40's) in the conversation, as part of a bigger discussion about the future disposition of the estate. Good or bad idea?
5. The town reassessed all properties a couple of years ago. Recent sales are running on the order of assessed valuation plus 10-15%, which gives me an idea of where to go.
6. At the price I'm thinking, I'll have a capital gain of $300,000-$330,000. Suggestions on managing both capital gains taxes (ouch) and avoiding Medicare B IRMAA. My wife and I are both 68, so in 5 years RMD will kick on on the IRA's.

Thoughts? Ideas? Pitfalls? I know conversations with both a good Real estate Lawyer in Maine, and a CPA are both in the future.

submitted by /u/MiserableCancel8749
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source https://www.reddit.com/r/RealEstate/comments/1w55y93/vacation_property_saleopportunity_or_pitfalls/