I don't think payment method has any bearing on giving a 1099 or not? 

You'll pay more than you think. 

I think this is a highly doable investment scenario for your family and I recommend it.

Just thinking out of the box.

G'Day Carlos,Personally, I think it's a recipe for disaster rehabbing from out of state.IMO you would need deep roots in the specific market you are looking at investing.Or years long experience of knowing the who, what and when in that specific market.I only know of a handful of folks that can do it successfully and even they have been at it for many years and probably still loose money on rehabs to this day, no matter how integrated they are with everything and everyone.A good resources for pre-purchase, during rehab and after rehab's is Inspectify.Always get eyes on site before buying a property or processing a progress draw for the rehab.Much success

I think maybe this is an ideal property for STR, but our family has only done LTR for years. 

As I would hear them speak, I would often think to myself "OMG...this guy is leading lambs to slaughter".

I think it's the type of property that I could rent for 30 plus days at a time if that matters. 

I think it's a mistake to start PM from scratch on your own.

Do you think the restrictive rent control is worth looking to buy in Takoma park if I can find something there?