Also, I imagine insurance might come into play as well.  

They need to be licensed and insured.

Also planned on managing it myself for a little while and putting it up on AirBnB for $165 a night. 19 days a month and I would break even (adding in insurance and everything else).

Additionally, good brokers can help set you up with some of the key partnerships you will need (mortgage broker, property management, insurance, etc.). 

@Kevin Tuttle OK but the multiple properties that I own are free and clear when a tenant leaves I have no fear I have no mortgage to pay I do my minor repairs find another tenant And go back to making the same return Copy paste repeat buy a new property free and clear find Tennant when they leave no worries I owe nothing other than taxes and insurance at the start of the year

Hi Everyone,Insurance has been a frustration for me as I'm constantly adding property to my portfolio and always need to go through my agent (often with a couple reminder emails).  

Many insurance companies will no longer insure a property using oil due to the risk of a leak.

I have a property that has a well: they're great for home owners but are a PITA for landlords. 

If the 2nd is compeltely upside down and someone wants to complete a sale then it's in their financial interest to try to recoup any funds that they can.Depending on 1st lien investor or insurer guidelines will determine how much money is allotted to suboridnate lien holders.

Maybe you can get an equity loan on your house or you might apply for a FHA insured loan that helps you get started.