I can’t see Phillip putting himself in such risk as to commit insurance fraud, he is a pig and a roach, and extremely crafty at conning dupes out of their allowance. As a bottom feeder, he’d never take on law enforcement and insurance. I’m sure he would sell his mother’s kidney if it meant an easy 10k, but he has his con on lockdown. He probably sold Leanna to Romanian human traffickers to replace his broken Guile statue...
As far as motive, I can’t think of anything about Phillip’s exaggerations that can be verified. No one will ever know (for now) whether he even owes a dime in taxes. His last tax con was to collect money to fly Kat back and forth and move her in. This mysterious 17k amount is probably just a slush fund for travel and retirement. This is probably a stage in his ‘long con’. He will always be in distress, he will always ask for money, BUT, he knows this con will run its course eventually.
As far as his house and CT vacation, I’d love to see Phillip get “Squatted”. Not Swatted, Squatted! Since he announced to his viewing audience that he will be out of town, it would be epic if a dozen of Seattle’s finest made Casa de’ Pig their home. Drill the locks, change them, move on in, write a false lease, and defile his loveseat (aka: masterbation station). When him and Kat arrive home they will immediately call the police, the squatters present the lease, and the police shrug and tell poor Phillip it’s a civil matter and it’s up to him to take this to court for eviction proceedings.
He would literally be homeless, without his possessions, and fubar’ed beyond belief. The eviction process would take anywhere from 3-6 months and cost thousands. Where would he go? What would he do? This chapter in Phillip’s 10 year begacy would make epic entertainment and I can’t think of a better con man to get conned.