Here is what I always consider:TaxesInsuranceManagementMaintenanceUtilitiesRepairs (reserve for big ticket items)Once you have accounted for those items then see if the terms you get on the loan are less than the remaining funds.  

Doing my twice-a-year visits (plane tickets, hotels, etc.) make no fiscal sense with the revenue from a single $40K SFR.

Just ask our last time share presenter. 3hrs later I had a free cruise package (upgraded the package at my choice/cost to a nicer room), $25 gas card, two nights in a Marriott, $100 restaurant gift card, and two tickets the comedy club. 

So is buying one lottery ticket and willing big.

More importantly, will these owners go to market with their properties after not being able to win the lucky ticket?  

However, Capital improvements which are a much bigger ticket and done less frequently can easily be much higher.

@Edward Zachary Samperio 5-10k in case that you incur a big ticket expense like an hvac. 

Airlines charge $500 for a plane ticket, then they tack on taxes, baggage fee, booking fee, and sell you a 3.4oz bottle of wine for $9.

I would like to get it now; however, when I recently got quotes it was more expensive than I was hoping for.The cheapest I found was through RLI for $370/year, but if you've had 1+ auto tickets then it bumped up to $500/year.

But I still require problem tickets in my maintenance software for issues so that stuff doesn't fall between the cracks.