Biggest expense appliances, hmm, this is not a deal, 

Yes, that is my biggest concern is the very poor cash flow - but with the area I'm in, I see appreciation being a large piece of the puzzle.

Some things that might be a concern:1) Obviously have to make sure things are all permitted first2) I don't want the room to "feel" like an addition, so flooring has to be same level/standardized with the rest of the house3) Unlike the rest of the house that has an identically-shaped 2200sqft basement underneath, this added space will not have a basement directly underneath it -- I'm not sure if this poses major cons for some reason that I'm not aware of4) Especially given the lack of basement underneath, I have to make sure that the HVAC can still somehow be piped into this room#2 and #3 are probably my biggest concerns (#1 and #4 I can find out relatively easily)Any tips/thoughts or other experience would be greatly appreciated. 

The biggest issue we had by far was the back neighbor.

Titles, being occupied are my biggest fears.

The opportunity to address the biggest need in our local resort, employee/workforce housing.

The biggest benefit is the ability to leverage and have the tenants pay the mortgage.

The biggest advantage of being an agent is having access to the MLS; besides that, if you have an educated fiduciary, I see no need to hire a realtor to represent you on a deal you have already identified. 

One of the biggest mistakes I see other investors make is not protesting their taxes every year regardless of if there is an increase or not.

Choosing kitchen cabinets is probably the biggest is not the most nerve-wracking decision for your kitchen.