Normal Screw down roof valleys are about a foot wide and this is about 2 foot wide, using my fore arm as a gauge.

For a reference to size, that's a standard 12 gauge shotgun shell in the center.

Question is- Should I contract an agent so she can put pressure in adding upgrades or bringing down closing cost or thats not going to work in today's market?

Really easy to replace too, as long as the right pressure sensitive adhesive is used.

Should I hire a realtor to pressure them for upgrades or lower closing cost?

The new manager might help put some pressure on getting everything transferred over. 

I don’t have any short term rentals, but have gauged turning my Florida home into one when I leave and the market is still there.

The pressure on housing will only push prices up.

Many folks from out of state leaving their own high priced markets to come to Denver where they may pay less but it's putting upward pressure on prices. 

Now take into account, there may be years where you have to use some of this cash flow to maintain the property.Overall, this is how I run the numbers at a higher-level overview and gives a good gauge of what to generally expect.