With the cash flow play you need to buy low, negotiate hard on price, expect no appreciation and get a very healthy cash flow, nothing marginal,  And expect when you sell to make little to no appreciation, then any gains are icing on the cake.

So, if the value goes up 2% you gain $20K on a $500K in equity or +4%.

If you think the culture in Atlanta GA in a class C or D neighborhood is the same as your culture in Boston in a Class B or A neighborhood you will find most likely that they do not match up.

After you gain some experience you should start buying in a cheaper market, like Ohio.

It was well worth it since I had monetary gain, but I also learnt a lot from this project!!

Fix up the house and sell it and put the equity gains into a multifamily house.  

Any suggestions on how to legally put Damage Deposits into a CD to gain interest? 

I purchase multifamily all the time and when I walk properties, I always inquire with the tenants to gain an understanding of the property.

Generally I think planning for 20% vacancy when starting out is smart as it can take some time to get traction on your property and aiming for 1.5 to 2 times the LTR rate. 

I have always been weary about investing in this area even though on paper it sounds like there is a lot of cashflow to be gained!