My first house was given to me by my father in law as a wedding present, so I never had to work out all the math on it.

I'm familiar enough to know what the scope of work is and what the process should be, so my initial thoughts were to sub all the work out and have them pull their own permits for each job. 

Even if it doesn't work out there are lessons you will learn in the process. 

It will undoubtedly get very expensive and annoying quickly if you have to hire all the work out.

Like 30 years.....which will work out great when I get those 30 year mortgages.  

i think 4/2 is better or a den/workout room. 

Then you find a brokerage to work out of.

How did it work out for them? 

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

If @Muju Hussain finds a property and teams up with a developer who has his own team that may workout as well.