But why not try earlier and start gaining some income outside of our W2! 

Starting out, I had a list given to me by my realtor at the Short Term Shop. 

That's how I started - renting out a spare bedroom to a roommate and I still do that because once I learned I didn't have to pay my whole mortgage it was hard to imagine paying it all myself again, haha!

It’s seems easy to believe that you’ve considered everything, especially when trying to put the funds together for a big project and eager to get started.

Then you can start digging into utilities/etc that might be large hidden costs many don't realize are needed.  

Unfortunately, some Board members are creating friction and preventing the process from starting. 

If you start filling up to quickly then you might be too cheap. 

I'd say go for it, everybody has to start somewhere.

 So if an agent is not strong in using social media, are there services they can outsource this task to?

Then you can start over.The other LTR lease is in place until it ends.