Is the grass greener on the other side? 

I wanted to just walk away from my career in 2017 as well when I was 27 because I was fed up with my role and wanted to do the full-time real estate investor gig, full bore. 

Unraked leaves, tall grass, cars with no tags.

That said I’m spending probably more than the average TK buyer doing research, so either I will go all the way and put together a deal myself or I’ll get fed up with it and give up, as I’ve done several times over the past decade.

I have renters ready to move in mid February at $2,500 they cover all utilities, snow removal, and grass cutting.

From cutting grass to major repairs I hire professionals because of lessons learned.

I've seen posted on the deal makers list that these 2 credit unions will do HELOCs on rentals;   Pen Fed and Navy Fed. 

For example, each bathroom should be fed independently with their own 20amp circuit that feeds Gfci outlets.

If you don't mind spending some $$$, then Canton, Fed Hill, or Fells Point are good neighborhoods for young professionals.I'm looking to househack myself, but because I have kids we're looking for areas with decent schools and some trees (ie in the county).

By that logic, if I wanted to stop mowing the grass at my rental and have my tenant start doing it, it would be considered a rent increase because he might have to go out and buy a mower (which would be an increased cost to him).