When you say you reject 50% of requests, Is this due to lack of message or not finding common ground with the requesters?

Because of lack of knowledge or someone showing them wrong way.

It was so bad, my agent's manager stepped in and basically said they would only proceed with the property if I signed additional documentation stating they were not liable for anything that happened with the house, being fee's, lack of inspection, and more.We obviously decided to walk away.Good luck!

Dreams are only foolish to those who lack them." ~ Peter Reese

Unless the property is owned by a LLC or Land Trust you will be identified as the owners through the tax assessor anyway if they really look into it.Cons- You are negotiating from a position of weakness if you lack the firmness to say "no" and enforce the lease.  

My lack of including utilities leaves a big void, but like I said, it's something I don't even know how to estimate too well right now.

Combine that with a lack of cash flow and this is a losing proposition.The price-to-income ratio is already in excess of 13 so you have to ask yourself how are prices going to triple or quadruple in 20 years?  

Maybe this would be a question for my Real Estate Agent but she is a friend of the wife and seems like here experience is lacking outside of traditional sales

Rents are hot too - I have a four-plex in a prime location coming up for sale that will need serious work, but given the recent lack of ceiling on rents lately we might be able to make some numbers work. 

Thanks for the reminder that it's apples and oranges with the leverage that RE provides compared to the stock market.