What makes it even more frustrating is that I see/hear about this all the time.

I can't afford to to give both properties the attention they deserve  and I'm not sure I can get top dollar if I  cut corners.

Home Depot makes a $40 weed whacker that uses the same 18V battery I have in my power drill, so the frustration associated with maintaining it is minimal.I would second the wood chips, fake grass, and would also throw in pebbles or gravel.  

If he were to respond, I honestly have no idea what to suggest as a fair and affordable deal.

I don't really have the money to spare, but I certainly can not afford to lose any money on a bad deal.

So the following is a list from my experience, that you need to a) plan for and b) understand how to deal with if you're going to get into RE in the city.Tenants (non rent controlled / stabilized): there is a massive shortage of affordable housing in the city, and a shortage in homeless beds as well.

The third move would be to find an affordable flip and jump in to real estate investment aiming you enjoy it. 

They are usually fresh out of college with lots of debt--- that means they can't afford a mortgage.- Why buy a house you have to all the work on yourself (mowing the lawn, watering the grass, etc) when you could live in an apartment building with an on-call maintenance man to do the work?

For the record, I live by myself and have a great job, so I can afford to "house hack" and move around easily.

A year ago, the average 30-year rate was 4.12 percent; the 15-year average was 3.22 percent: http://abcnews.go.com/Business/wireStory/average-us-rate-30-year-mortgage-rises-408-32182467 Affordable Housing, Racial IsolationJustice Anthony Kennedy delivered this timely message in the majority opinion, ruling that the law allows plaintiffs to challenge housing policies that have a discriminatory effect — without having to prove that discrimination was intentional: http://www.nytimes.com/2015/06/29/opinion/affordable-housing-racial-isolation.html?