Leave you with one last question: Does your reports from any software tie in to exactly your tax return? 

Obviously the HOA is keeping values in this neighborhood down because an owner would have a mortgage plus another $715/mo for the HOA, which only covers use to a community center but nothing else.Besides holding costs, is there anything else I should be concerned with for a flip on a land lease? 

If it was long term yeah you can make it clear upfront as a take it or leave it.

Man, just in 3 years if you have the tenant leave every time, even without the negative cashflow, that alone can cost you an additional 20 or 30k.

Let’s leave the magic to the magicians 

@Frank Hotard How much will it rent for when you leave?

And even if the tenants chooses to stay in your property for 2yrs, the damage they may cause will eat away all of your cash flow and leave you potentially upside down.

Let me know if you ever have questions/concerns.

Despite having generous incomes, some of them are utterly irresponsible with the property and leave a disaster behind when they move. 

@Andrew Slezak I recommend you first articulate precisely the liability events or concern which are pushing you to transfer the property to an LLC.