Recently we had storm and blew off the roof shingles off, we have a roofer came out and checked he found couple spots hail damages.

We got a bid for $4.20 per sqft for everything minus roof shingles.

Turns out elm is very dense wood, so the extremely heavy branch ripped off a corner of the neighbor's house on its way down: shingles, gutter, soffit, fascia board, even the framing of the overhang lookouts and some of the siding.

Found a 4-plex in residential area (population <3,000) about 45 minutes away.Purchase Price: $92,000 (MLS) Bank Appraisal: $99,000 (appraised "sale" value)Mortgage: 20% Down, 5/15 ARM (self-employed, first mortgage)Rent Roll: Full occupancy = $2,050/mo; currently = $1,630/mo (3 units with long-term tenants, studio unit vacant)Roof: No leaks but needs shingles in 1-3 yearsHVAC: One gas boiler, hydronic/radiant heat and hot water; no ACOther: 2500 square feet. 

The second property I bought, I knew it needed a new roof, but I was trying to put it off as long as possible.. multiple layers of shingles and some missing.. blah, blah, blah..

For example:ROOF - Asphalt shingles should last 20-25 years.HVAC - I usually plan for a lifespan of 15-20 years, but your dollar amount looks accurate. 

Current condition: The Good - Shingles and kitchen are about 9 years old and in great shapeNeeds: Foundation needs bracing, mortor work, drain tile, (basement is not tall enough to be considered living space, any ideas?

The shop that is on the property is at least a 20x50 shop (this is a BIG shop) and the roof has shingles and wood siding.

You probably shouldn't be ripping off shingles to replace roof decking as your first DIY job. 

Definitely cheap vs shingles!