But I think we face a very different landscape in '17 than we did at the end of '07 or '08.

Is the landscaping kept up?

Don't forget landscaping.  

Most landscapers keep their equipment and staff busy in the winter doing snow removal.

The demographics are going into the stratosphere.

. - $300Tax - $1103Misc - $240 (5%)  Landscape/snow removal, pest control, etcRemainder = $1,517P & I - $2045.26Future Cash Flow = ($528.26)Less Rent Unit A - $2,000Current Cash Flow = ($2,528.26)Your P & I (Mortgage payment) would need to be around $1317 in order to Cash Flow $100 per unit.  

The vacant piece has water run off from a slope which owner has nicely landscaped with decorative bridges.

It went something like this: start small with something that makes you money while you sleep; an example was to start with an empty lot and let people park their cars on it to sell them, then from the income you upgrade fencing areas for park and store small businesses like landscaper's equipment and people with boats or RVs are likely candidates, once that creates enough money you can upgrade to actual storage units.

_r=1&Deciding between Charlotte and Philadelphia was challenging, but this is how I did it: Step 9: I pulled high level statistics from Trulia, the census bureau, and the Bureau of Labor Statistics (college educated percentage, commuter percentages, house hold income, median age, home owners percentage, marital status, crime, 1900 to present population growth, 10 year jobs growth rates).Charlotte won out on household income, less crime, population growth, jobs growth and more college educated peoplePhiladelphia had more renters, less driving to commute, more single peopleI also pulled approximate rents and median home prices by neighborhood and Philadelphia won on better cap ratesStep 10: My final decision: Philadelphia Philadelphia is also closer to NYC (2 hour train ride), has improving demographic trends (gentrification), more affordable for my budget, stronger rents, and larger urban center with more investment options (SFR and MFR)There are obviously downsides such as older buildings, higher crime rates, historical population growth issues We can debate the merits of one city over another, but eventually one has to get off the proverbial pot and make a decision.

@Brian Oswald Try Great Lakes Landscapes and Snow Removal.