I remember one guy in the S.F.Bay area that found a site for a new Pepsi plant when Pepsi was unable to find one and made a very large finders fee, his mistake he got involved in the deal to far instead of stopping at the introduction phase and the Pepsi lawyers used that to not pay his finders fee, but only waiting until it was almost time to pay him and the deal was basically done.

What I'm thinking about is to combine bedrooms 1 and 2 into a large primary and add a full path adjacent to the current full path. 

I'd also have a hard move out date along with the lawyers (or whoever handles your closing-I'm in Canada where it isn't always the same as the US) holding back a large enough amount to get her to move out on time and leave the place in good condition.

if I am holding onto this property for a long time, will 1 year of lower income make a large difference?"

But I'm not sure what that has to do with carrying a large mortgage where you are just breaking even and speculating that property will continue to appreciate.  

So our cash flow was reducing during our hold due to poor ADR increase and large insurance and prop tax increases.  

This works best if the lien holders are a large bank.

I know there are large property management companies that manage properties everywhere, but I am curious how they overcome all the challenges of not being near the properties.

This influx is largely driven by young professionals and families attracted to the city's burgeoning tech scene and quality of life.

If there are a large number of openings, then they are likely filling that need with travelers.See how much the property will cost a month.