I love not having to take that"the drain is plugged" phone call.

@David McCracken In this case stopping the water might be the easy part........... install elbows on the down spouts and lead the water about 4 feet from the foundation; install a French drain around the foundation where the soil is the highest-usually 3 sides and lead the water away from the building.

If it has the iron/metal drain pipes under sink then they tend to corrode with rust and then collapse when you get water turned on, which means you now have to replace all of that with PVC. 

I can imagine what you are describing, I am afraid of the drain on cash flow by maintenance and operational management like you describe. 

My question is, do i spend $50k on the basic pool in back yard or buy club house with everything for $50k, its only about 1 block away from our house.

I get a ton of telephonic solicitations from folks claiming to be HML, I just block the number and move on.

(If this is me being colossally stupid, please let me know)The duplex is in a good area of the city, near a really good park, 2 blocks away from the main road through the city and situated right in between both public and private schools.

I live here and invest here, Indy is block by block.

I have a land which had percolation test saying the pits observed is unsuitable for a standard type individual sewage disposal system without the addition of a curtain drain.

(The other side has a cinder block wall).