The property was finished and listed in March for 369,000 have dropped the price monthly and I am now at 320,000.

I guess Feb, March isn't the worst time.Are you in the contractor business? 

The tenant is in place until March 2019.

-I rented it out from March 2016 until present.

If I blindfolded you and dropped you on the other side and told you that you were in Hanover, you'd be impressed with how nice Hanover looks.I'm told that the Mayor has an official plan to march that demarcation line further to the east. 

Host an event highlighting the haunted stuff. have a dark metal band or weird steampunk band play the event. 

The question I am wrestling with and I am literally out of my mind thinking about it - shall I rent the current home (A) and hope that the property appreciation will make up for the lost savings and more (build a asset and income stream over time)  or should I sell it (A) and invest the proceeds in (B) and bring down the monthly expense. 

You need to do something soon, by the way because I would imagine Milwaukee is like Cleveland (Which is where most of my rentals are) in that you do NOT want to try to get renters from November through March because of the cold winter months.Either lower that rental price or.........you may not like this.......but advertise on GoSection8 for Section 8 tenants.

March rent paid on time.

I moved to Phoenix, AZ in March 2017 from Miami, FL with my girlfriend after she got a new position, and immediately got my Real Estate License (former career in college athletics).