I notice a lot of competition from beach front condos of the same size. 

Send me specifics about he unit, size and what you need done.

Landlord tenant law has its own version of ambulance chasers that would love nothing more than to make a few bucks off of a landlord that tried to read further into a tenants life than just criminal history, verifiable income, credit score, and rental history.Logically, we would all like to be able to make decisions based on personality differences, family size, possible income drops, or whatever gut feeling we have.

In my expierence that is all going to need to start with a well crafted chart of accounts. 

I will also have a FT job, at least until I can replace my income....We would need to raise some capital / find partners because we couldn't afford a down payment of the size we are thinking by ourselves.Looking to network in Maryland!

I have a larger portfolio (65+/-) units varying in size from 300sqft - 7,000 sqft and that affords me some leverage on our cleaning vendors. 

CA when some of the larger big lot subdivisions were platted these were 20 to 40 acre in size.. many times you would have remainder parcels on the borders I bought one that I think was 75 by 2100..

The idea behind this isn't novel of course, but a way to circumvent the endless and crowded sea of opinions and narrative shaping charlatans that make their daily bread by deluding the curious minds of some vague one-size-fits-all approach... but oak trees don't grow over night. 

I own a property similar in size and in the same area.

Chart that out over increasing property values, you'll find a sweet spot that will be about twice of what you are considering for most midwest markets (certainly for Milwaukee).