I work as a network Engineer, and i have a decent income but i don't have enough employment history in the united state(I was in Dominican Republic since i was a teenager)  so i don't get a approve. 

I want to fix my past teenage mistakes and better my score.

We also spend a lot on pool maintenance each year, and have teenagers that like to throw chairs, etc. in that we have to replace.It's a mess.

I am married but she has her plate full with a full time job and raising our 2 teenagers.

A very good friend of mine that I've known for many years and I have been discussing real estate since we were teenagers in high school.  

I am a single mother of two teenage boys and I bought a vacation condo in Conway NH for us to be able to enjoy.  

Or do I get the dumpster and let my teenagers have sledgehammers, gloves and let them go for it?  

One bathroom with multiple teenagers was untenable.

I guess that depends are they teenagers?

Having said that, I wrote the following, candid, hopefully not offensive, summary based on the likely perspective of a young family (kids on the way up to teenagers), 25-40 yr old professional, or DINKS (dual income no kids).