If you had an average property that remained in decent condition, it’s worth 5-10% more annually in year over year appreciation.I wish I’d bought a $13m 65 unit multifamily in center city philadelphia in 2013.

That price is normally adjusted for annual maintenance costs (roughly 8% per year).

but immediately tracking/recording the business expenses under each LLC in a ledger and filing away the receipts for our annual tax preparation.   

Make sure to read up on the tax exemptions, they usually require that you are a resident of that state and file for the exemption annually. 

What is he currently receiving  for monthly/annual rent for the property?

I just closed on a duplex that had an annual premium of about $1060 through Foremost as an all cash value policy only.

I do not pay the annual fee on VRBO.

You can do a simple note for private money with annual interest payments or even monthly interest payments if you want to go to that much trouble.

When we aren't there, we would definitely rent it out for weekly rentals.Numbers:Have up to $100k to invest in this Duck propertyConsidering homes in the range of $750k-$800k that attract around $70k annual rental income.We know that we will likely only use the property in season for a week or so, but we would be using it more out of season.Any reactions from investors who have considered this/similar situations? 

The DSM Metro does a nice job of keeping clean and hosting multiple "touristy" events annually... for which the locals EAT UP.