I do not like all the bubbling up you have, it looks like it is failing or was never installed right. i would replace it. i would negotiate the sheathing price, at 2.50 / sq' they are charging $80 per sheet to replace a 4' x 8' sheet. make sure they secure the top edges of the roof when they bring it up the walls with a metal strip anchored into the block, this will keep it from coming down like the first picture. and i would agree with the size gutter and downspout they recommend.

The problem with CT unlike MA or IL is that it doesn't have an anchor metropolitan economy like Chicago or Boston as @Jay Hinrichs made a good point.

For me it all comes down to location, unique feature or anchor, ease of releasing, and traffic counts.  

With Kennedy King College buying land and expanding as well as BNSF Railroad, a 50 million dollar infusion from state and city funds, along with anchor stores Whole Foods, Starbucks, and Chipotle, Al and Heidi were able to secure a buyer at full list price 215k even before they had completed the rehab!

I'm down here in Texas and through exploring the local area I have found a number of nicely priced duplexes near a military base which got me thinking; Is anyone here willing to share their experience owning rentals i...

Dark stains like walnut are richer and add elegance as well as help to anchor and showcase furniture better as long as the furniture is lighter tones and color.

Madison is anchored by UW healthcare industry and state government and those drivers are not going anywhere. 

Otherwise, call up one of a dozen hard money lenders, Anchor Loans is a good example (I am not affiliated with them in any way shape or form) and borrow money from them at 8-10%.

Some Updates On Texas real Estate From Recon.IKEA assembling first South Texas Store In San AntonioWeitzman will develop Live Oak Town Center, an 830,000-sf retail center anchored by South Texas' first IKEA.The project at the southwest corner of I-35 and Loop 1604 will include the 300,000-sf IKEA and 530,000 sf of other retail space.

Among the biggest projects anchoring the boom: The $524 million Bucks arena.Northwestern Mutual's $450 million office tower and $100 million apartment high-rise.The $137 million BMO Harris Financial Center office tower.The $122 million Couture apartment high-rise.The $80 million conversion of the Warner Grand Theater into the Milwaukee Symphony Orchestra's performance hall.The $50 million Westin Hotel.Large projects already completed over the past year include the $101 million 833 East office building, the $53 million latest phase in The North End apartments and retail development, and the $52 million Kimpton Journeyman Hotel.Finally, there are several new and ongoing downtown-area developments below the $50 million mark, including apartments, offices and hotels.Of course, Milwaukee has it's challanges too.