There is a river behind my property and the town / state required a wet land scientist to preform a survey to identify the "high water mark" which was placed at the edge of my property. 

However, this would increase my costs by about $4,000 a month (about 3K would be spent on skip tracing).I'm also exploring the idea of wholesaling in other states instead of in Northern Virginia and south part of Maryland.

If you are not then you will see a ~$10k foreclosure sale, a resale less than a year later to an unwitting out of state investor for $50k, and the current attempt to sell it for $58k to get the current poor bastard out of the deal and cover the cost of the sale.Be very wary of becoming the next guy holding the hot potato when the economic music stops...I see rent rates have stopped rising and our local MLS shows an increasing number of days on market so I feel the music is slowing.Hope this helps!

And while we do have many more out of state "eyes" (buyers), it still fees like a fresh market with plenty more to offer.

Not stating this as a stereotype; just from experience. 

https://www.biggerpockets.com/users/ZacharyCole/referenceshttps://www.biggerpockets.com/forums/92/topics/518583-feedback-on-renttoretirement-and-zach-lemasterhttps://www.biggerpockets.com/forums/92/topics/765347-rent-to-retirement-reviewhttps://www.biggerpockets.com/forums/850/topics/895660-my-first-investment-property-an-out-of-state-dealhttps://www.biggerpockets.com/co/RentToRetirementhttps://www.biggerpockets.com/forums/92/topics/929410-rent-to-retirement-updates?

I have been editing it based on a state-specific lease template which contains 15 pages.

Currently, we have a commercial policy with State Farm but when our lawyer reviewed it, she recommended we increase our medical liability coverage.

Your state and local law may have some mandates that you must follow regarding treatment of those funds.

This strategy will also give you a far greater appreciation of traveling in off peak seasons, which as others have stated, is the only time you’re traveling to your vacation homes for “free.”