So If your are still contemplating this as a rental I would definitely raise the vacancy to about 1.5-2 x's the monthly rent.

I am contemplating on going the FHA route but would like to have a better understanding of issues I may encounter. 

This hypothetical best rate but slowest process lender is going to make you contemplate suicide with the hoops they make you jump through.Do not try to generalize based on those three scenarios.

I am contemplating just such a thing in the next year. 

Junior liens have some considerations to contemplate due to the priority in title they hold.  

Not happy about that, and coupled with other issues, i'm seriously contemplating taking this over myself. 

I am contemplating a flip to generate some capital for future endeavors and I see a huge opportunity to flip in the Belmont neighborhood.

It pisses me off when i have had to do an eviction, and then I contemplate suing them...but then somehow (even though I use a managment company) lenders find out Im the owner and they start calling me and asking if I have seen so and so, and what kind of car (etc) they are driving.

I contemplated self managing when I purchased this property.

I have contemplated working at a realtors office that is privately owned.