The property is in a popular location so I have experienced significant appreciation since buying it and the debt pay down is great, but it will be the only property I buy with a 15 year mortgage. 

The location makes it desirable for retirees and people trying to get away from city life while being close enough to still have a "real job."

That will avoid probate in case of your death.Create a single member, manager managed, LLC for each property in the state where the property is located.

I've read that you can only have one FHA loan at a time but there are a few exceptions (specifically around job re-location). 

Location Purchase Rehab ARV Etc....

May depend on where it is located.

You'll notice that you report no location next to your name.

The property I would be renting to them is located in Worcester, MA and commercial rates look to be around 12-14/sf.Thanks in advance!

The comps in the area are lower than the ARV NOW.BUT I WOULD KEEP IT FOR MY PRIMARY RESIDENCE, AS THE LAND SPACE AND LOCATION IS GOOD AND WITH TIME MY CONSTRUCTION COMPANY CAN FIX IT SLOWLY.PLEASE ANY HELP TO STRATEGIZE THIS WOULD BE HELPFUL.

Keep in mind many mom and pop landlords are very hands on.. and have to collect rent in person.. and as stated above it all depends on your location and tenant base.. like west coast tenants by and large you could automate them.. lower end C D tenants no way.