@Ethan Cooke I'm not as familiar with 30+ day stays, as the city we have all our units in permits short stay as long as you pay a 7% occupancy tax. 

(I am not an attorney nor is this legal advise but was involved in my own family probate action)

Mostly likely you will not have to pay any gift taxes, but you will have to file a gift tax return.Also, your son would be legally entitled to his share of the proceeds. 

. ($50mil / $150k) GF currently is offering around 20 loans/month so they can certainly reach their legal max in short order.

I realize that once I pay the legal fees, I'm effectively ouut that money.  

Also, she paid for the entire year up front, in the event that she was evicted, I'm not legally obligated to refund that money if she was in violation of her lease, correct?

income, revenue to the state/county, these properties are less likely to be eye sores and can/will help drive up property values for neighbors (catch 22 here)...etc.i live in rural area on Maui and have seen my share of legal and illegal VRs pop up...i don't really have a dog in this fight either way, but would probably like to dabble in this market as well should the rules/laws change...right now the process here on Maui is just too cumbersome (probably that way to make it unattractive) to become a legal VR property.I do wish you luck and ask that you post back with your findings/results for the other Hawaii folks!

It may not even be legal in your neighborhood.   

The borrower must have held legal title to the lot for at least 6 month prior to the closing of the permanent mortgage for cash out. 

Once you go to court you need to provide proof/documentation that they are behind on rent and any other legal documents pertinent to the eviction.The state then gives the court 10 days to schedule the set-out, unless landlord & tenant agree on a different time frame.