My friend is moving in the next couple of month and was hoping to sell the trailer and go on a small vacation with the money.He just found out that the person who was appointed to transfer the sale to my friends name never did and he even apparently lost the contract that he the church and the previous owner had made.  

How would a person evaluate a property for the purpose of renting it as a vacation rental? 

I'll also mention my financial planning thus far has set me down the path of having an emergency fund (~6 months expenses), vehicle repair fund, vacation fund and even general savings fund, all of which a portion of my biweekly paychecks direct deposit into.This probably all comes down to personal preference but I guess my main question is this.

I've had this situation happen before where the seller had no money for a new place to live so we held back $5k that was to be released once he vacated the premises.

I’m currently out on vacation with limited internet access

For those of you who has listings on AirBnB,  HomeAway, VRBO...etc. You might want to click here to put your vote in and make sure your voice is being heard. This link has made it easy for you: https://actnow.io/xKhnQ...

I send a Termination Of Occupancy and Notice to Vacate to the Tenant in 3 ways. 1.

Ask to interview other realtors in the same firm who would not be going on a five-week vacation - and have the listing contract reassigned. 

Future retirement homes or vacation properties - some clients with 1031 into wonderful properties a year or two ahead of retirement. 

You are just taking a vacation or two in April and May.