I currently am living in a single family home that would rent for 1800-2000$ a month if I chose to rent it long term.

I have a duplex that I originally intended to have serviced by individual heatings systems, but ended up installing a single system that's large enough to heat the whole building.

He is not financially independent, but I bet he's living the life you dream of.Figure out what you really want, then start building a plan to get there.

Lots of crime over there, I'd say best bet would be 1 occupied and 1 vacant.

With C or below you probably can't avoid some of it so I'd go with a recency bias, ie anyone who has a long period of time between their last eviction and successful rentals other places will be a safer bet than the guy that just got evicted. 

We have a lot of cheap single-family homes in certain parts of Milwaukee and they have an irresistible appeal to new investors!

One tip: don't force yourself to stay in single-family, but sticking with what you know best for now is good.

I would consider single family homes as well but multifamily is the ultimate goal.

There are a lot of options for all in one stacks (washer dryer) or a single wash/dry machine as well as small size (18") dishwashers.Don't skimp on these sorts of amenities.

Recently, I was debating whether to lock in the mortgage rate for a single-family home we're purchasing in December, especially with rates spiking recently, or wait until after the next Fed meeting and election to be finalized.