I'm assuming I would have to pay it off if I won the house. 

OMG, please do  NOT take money out of your 401K to pay off a mortgage, especially not for a rental. 

That being said, I'm always an advocate for paying for mentorship to fast track your goals. 

am working with them now and had the first policy (with Spinnaker) cancelled for nonpayment/late payment so we rewrote another policy (with Millenial) and having the same payment problem again but at least they are communicating that cancellation is coming. they want me to pay by credit card over the phone so the payment wont be late and cancelled again. but when i go to mycoverageinfo.com to check on status it shows its been paid.

I have no problem paying a wholesale fee if there's plenty of margin for me. 

The seller's LLC pays capital gains tax and depreciation recapture, while the buyer's LLC uses the purchase price as the new cost basis.

You can pay for expediting for plan reviews and the best way to "expedite" beyond that is to make sure that your engineer / consultants are submitting complete packages each review cycle.

Withoutknowing the details I can not suggest which would be right to add on.Several you should pay attention to are:- Ordinance & Law: Provides additional building coverage to deal with rebuilding costIncreases due to changes in Zoning or Building laws- Personal Injury Liability: Libel, defamation of character, wrongful imprisonment, etc.

After talking to another family member they said they would be willing to go in on the duplex and offered to pay the $40,000 down payment and help with any repairs but they want to be "partners" or "own" a percentage of the duplex.

@Shayan SameerThe non-paying tenant could impact your short-term cash flow, so consider the potential costs and timeline of eviction in your state.