The Survey
Here is an overview of the property and current layout just for familiarization. I sent this to a few vetren operators so they might be able to best advise me on what kind of antenna(s) to put up. The best advise came from Mark KC7JOG who recommended a Maypole.
House front view

Front View, House faces about 10 degrees west of north,
Front north west view

Front Right side. Notice the power/cable/phone lines. Unfortunately, this lot has high voltage power lines on three of the four side. This ended up being a very noisy environment. It also limits the height of anything that could fall into them.


Front north east view

Front Left view. MFJ-1798 vertical at 20 feet is visible in the side yard. Four lanes of heavy traffic on left side. The house is on a corner lot.

 
East view

East side of house from other side of 4 lane street. Notice MFJ vertical and a scanner antenna to the right at about 20 feet on a 40 foot telescoping mast.
South east view

View from inside the east side fence (south-east corner of lot) looking across the backyard. Fence is about 70 feet long.
South west view

View from south-west corner looking at back of house. You can see the top of the MFJ-1798 vertical and scanner antennas. Also note the location of the chimney.
Looking at south west corner

View from roof at chimeny looking down towards back south-westcorner. Possible 30' to 40 foot mast installed here and run inverted "V" to this corner and to the south-east corner at other end of back fence.


Looking at south east corner

Looking down to south-east back corner from chimeny. With a 40 foot mast here, the antenna leg will clear the roof and connect to the back left corner. I can fit a 102 foot antenna in this manner.
Looking over roof to south west

Looking from roof over house to south-westback corner as seen from the location of the 40' push-up mast with the scanner antenna. Current thought is to remove The scanner antenna and replace it with an ARX2B 2m Ringo Rager and an ARX450 70cm Ringo Ranger. I can fit a 90 foot antenna (like a BWD-90) from the top of this mast to that back south-west corner.
Looking along east wall
Looking down the east side of the house from the scanner mast towards the south-east back corner. Notice the used LM-354 tower lying dead on the ground, The hope is to install this just on the other side of the A/C unit. Permit pending. The MFJ vertical will be removed when/if the tower is installed.

My current hopes are to Install the tower supporting a tri-bander of sorts, a 6 meter yagi, a 2 meter yagi and topped with a small vertical of some kind. I would like then to have a wire antenna to cover 80m and 40m. I'm thinking the wire antenna could be a multi-band type to get more bang for the buck as well as optional choices to the tri-bander.

Options I'm considering are to use a B&W BWD-90 to go from the scanner mast down to the back south-west corner. Or install the chimeny mast and use a multiband dipole as an inverted "V" down to the right and left back corners of the lot.

I currently am using a Kenwood TS-2000 and would like to add an amp at some point. I am legally blind and am trying to get as much of this done now while I can almost see what I'm doing. This means I would like to buy, and not make whatever antenna(s) I will use.