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

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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.

Most tenants do not mind put their own resources but want to remove them upon vacating.