That said, so long as you keep the rent the same I have found the overwhelming majority of tenants have no issue voluntarily signing a new lease with you once you acquire the property.

You can sweeten the pot and pay them 1%-3% of the purchase price.

Right, how many licensed pot shops and state sponsored grow operations are there?

It would be a true trailblazing move for a bright, financially-forward-thinking young lady looking for her one true and perfect soulmate in life to tell her handyman beau to s**t or get off the pot before she takes on legal liability for paying for the full mortgage on their first triplex.Because there's zero chance the beau will call up the stairs one fine morning, "Yeah honey, going out for a pack of smokes, be back soon!"

He also has her security deposit, and it seems unlikely he would be willing to return it voluntarily. 

Or, keep the HELOC revolving as your Cap Ex well and instead of saving each month you use that to pay it down..it's all semantics in the end and how you think about the 'pots' you are pulling from

Most food servers, exotic dancers, and bar tenders, have very minimal 'base' income, it's mostly tip income, and a LOT of the time it's under the table money that the person does not voluntarily report to the IRS and pay taxes on.So, not a solution for you today.

You might want to consider sweetening the pot to get the bad tenant to move, if they move out immediately. 

Apparently towns dont like to maintain abandoned roads unless they absolutely have to.. considering it is the only way in or out of the property it is their duty to perform maintenance  like snow removal and fixing un passable ruts/pot holes etc.

I of course have advised that they call the police, however they are afraid of him, too, and don't want to stir the pot.