In this situation it would be difficult to have your cake and eat it too. 

Another slight problem is living on the South Shore of Massachusetts, Real estate is on the higher side but also if I find the right deal homes 350 and under in my area seem to be selling like hot cakes.

They consider any appreciation to be icing on the cake.

Once you feel comfortable estimating these figures on your own, it'll be a piece of cake and you won't need to rely on a contractor anyways. 

The best way to have your cake and eat it too would be to find a 3 or 4 unit property that needs work, fix it up and refinance.

Think of them as icing on the cake. 

If you buy the right properties in the right market and set up the right property management, it IS possible to have your cake and eat it too - my A+ rentals in TX, for example, have appreciated nicely since I bought them and they continue to put a nice chunk of cash in my pocket every month. 

The ones that are beholden to the hotels and hotel workers unions, like Anaheim and Santa Monica, here in California will ban citizens from using their home to make a few extra bucks. 

If your at a banquet, how many cakes can you eat?

Appreciation is icing on the cake so to speak and you can't live on it until you sell w/SFRs.