I am now debt free, have a sizable nest egg, and am ready to take the plunge back into the real estate world.

Hey Jonathan - I would love to find some meet ups on the North Shore in MA.

I originally left to build my tech career/nest egg in SF with my mister, but now I'm back and looking for deals.

Hi,To replace roof one contractor says 14k (he says 40 squares) to remove and replace:shinglesventsroof boots3 sheet plywoodinstall matl drip edfge everything upto GA building codeTo repair below he says 700$repair 4 roof bootsreplace rotten woodreplace missing shinglesremove empty wasp nest paint piplescaulk exposed nailsMy PM say 7k (he says roof measurement is 30 squares not 40 squares and mentions other contractor who says 40 squares is lying)to remove and replace:shinglesventsroof boots3 sheet plywoodinstall matl drip edfge everything upto GA building codeplus synthetic underlayment and architectural shingoes (not 3 tab) and ridge ventsHow to know who is giving right quote and doing right work.what is meaning of the squares.When I know I need to replace roof ?

My set up is generally a Schlage lock on the front door and security cameras (i just google nest) at all entrances. 

I know I never got an apology for losing our family nest egg. 

The mistakes feature most prominently as the pain of failure and not making money lingers on for a long time while the successes fade pretty quickly.As to deal analysis I would have to say that as real estate appraiser - MAI candidate (member Appraisal Institute Candidate member - the course work and experience of appraising lots of types of commercial and residential property over 10 years or so gave me a solid understanding or how to look at various properties by the numbers. 

Quote from @Andrew Lax: So this is somewhat of a personal question.I am selling my Primary and moving to a condo on the beach - recently empty nest and dont need the space ... 

Recording is at the event link above.

Additionally, make sure to look at the risk involved as far as losing your nest egg, or part of it.Good Luck!