Another decision point here is what to do when it's time for me to look for my next home, do I sell or hold and rent out the rooms in the house to single renters?

Do not make a decision based on a proforma. 

4) Are there any other legal or operational issues that I need to be thinking about before making a decision?

Personally I don’t get how people can make such a huge decision like choosing an apartment to rent in such a short time frame.

Hudson, Essex, or union counties is what I'm really looking for..thank you  Congrats on making the decision man!

"create an open and welcoming feel" That priority could help lead to the decision to remove the scruffy border hedges, etc.)and top 5 for the interiorBudget for exterior and a picture Weather conditions locally throughout the year and sun exposure of the house's frontWhen you do that you will have a clear direction of what your working with and be able to direct your learning and searching.

As a policy decision though, they will not approve those for Section 8 voucher program.

I live in a very hot market (Washington DC area) and you need to make quick decisions to win listings.

There isn't even a thought or decision here... had they come to you with a heart tugging humanizing story at least there is a chance you might consider especially if you feel the circumstances extraordinary, or be upfront and honest about whatever hardship they are facing and perhaps you have a solution that works for everyone - but a threat? 

MLS is actually a pretty poor resource.