You can pay for a PMC system like Buildium, Doorloop, Hemlane, etc., or try to piece together several free systems.

With a large group of say 16+ guests a $2000 or $5000 weekend is much less expensive when multiple parties are paying.   

You can find a VA or a younger person to pay.

I would rather pay a little more now to build a foundational system for growth. 

This is with my contractor contacts who I refer out a lot and work below what retail pays. 

I actually did get someone, but then they tried to hustle us with a wayyy lower price when he went to pay

(On that type of deal it should but play it safe)Even if the seller can show you a current policy and that is what they are paying now you as the new owner may not be able to secure that same rate even from the same insurance carrier.

I ended up paying about 1/2 that with another service.  

Let them live in it and pay me a rent for a while, And then, offer to sell it back to them in 5 years at $1,000,000.   

You fail small.If it has extra land, then it can be a great deal, if the market needs more.