We would never extend a lease to a resident misbehaving like that.I'd encourage you to tighten up your procedures and, following your lease, get this resident out at the soonest possible time.

We were thankful to be able to pivot quickly and move the opening and closing events indoors (and even have to extend the closing event because of a jam-packed dance floor and people asking for an encore!)

Are the rental properties located in an area where there is no risk of extended periods of vacancy or large rent decreases during all economic conditions? 

Most multi participant retirement plans are Federally exempt from creditor judgements; IRAs are Federally protected as a bankruptcy exemption up to $1,512,350; some states (Texas, Florida) extend this protection to the full amount held in the IRA or any other retirement account.5.

Especially considering this performance is over an extended period of time.  

As of now, my general plan is to find a local realtor online who is experienced with real estate investing (and has investment properties of their own) to help me find a good local deal (goal is 20-25% return on ARV), get a hard money loan, aiming to rehab/repair/extend the property with my father (both have construction experience) within 4-5 months, and as for the loan exit strategy either sell or rent (depending on the deal). 

I tell them to sign if they want to extend and remind them if they don’t agree with new terms they must give notice by x date or those terms go into effect.

We only offer extended stays of 30 nights or greater.

We specialize in, and only offer, extended stays of 30 nights or greater. 

to be fair and balance like Fox news.. my client negotiated to leave 1k with them and extend the close until probate is done and get refunded 6500.00 so assuming they actually send him a check ..