By doing things the right way, great staging, great marketing, and really good photos, we have been able to maintain all 5 star reviews, which put us at the top of the list of available properties, and we stayed booked pretty much all winter.

How much cash reserve should I have for maintenance and maintaining each rental property

Across/on the street has about 3 or 4 large estates owned by Duke with sprawling lawns that will always be well maintained.

Then the guy with 100 acres has a road that runs beside the property and I thought that was a county maintained road, but it’s not; it’s his.

Let's just assume only the DP for a moment.If you put 20% down on a $100k property, you'd be out of pocket $20k...and would need to recover that cash, in the form of cash, before you started to make a profit.If you were only making 6% CoCR, and after the first year you maintained that same cash return through your cash flow per year, you would be getting back a whopping $1200/year.   

Residents would pay for rent for the land while they maintain ownership of the house.  

That space is for very well establish players, as the crowd funding platforms want to maintain their reputation by only listing properties run by strong and credible operators.

You know the work has been done right so it should give you years of relatively easy, maintainence free flow. 

It may be called Crystal Beach.This is from an agent.....Example of a Listings in Crystal Beach with a Positive ROI and very low HOA generating over 80 K in Gross Rental Income (GRI)The up side is you generate more ROI (see attached rental History ) the down side its not Gulf front and you must pay to maintain the property like the pool and the yard (see the Cost to Own ) attached.

As a landlord you have a duty to maintain the property within a reasonable timeframe of being notified and if you do not then the tenant has the option to not pay rent.