Why don't you share your info and your background and how many deals you have done in the land game.

The real estate game is all about relationships and strategies, and this is one of the most important topics to get right early on!

Renting to people that aren't friends can be great, but also, one tenant can make everyone's lives miserable, so that's why I start with short leases in the beginning. 

Sometimes you have to step back, really think about your long term and short term goals, stick to a daily, weekly, monthly and yearly plan.

If your concern is cashflow, then your concern is about being short of cash at some point.

The people that I see that have made their investors and GPs themselves real long term wealth, never anticipated a huge short term return.  

They have more skin in the game then you do.Make sure you get clear title.

Why I would agree, it would be ideal to start one ourself but to be profitable at PM it seems to be a numbers game.

The key is to understand the capital stack, who is in line in front of you and what are their terms.The people who are getting burned may have known there was debt in front of them, but did they know it was short term or variable - did they know all the details to make a good judgment on the investment.If a property had 20 year fixed debt at 70% would you take that over 3 year debt on a variable rate at 50%? 

@Jonathan CooperIf your current accountant is not familiar short term rentals and/or cost segregations, it's time to get a new accountant.