Landscaping was a challenge.

This topic has been around forever, but it's now 2019 and the landscape continuously changes. 

There is the option to do it without that, depending on what kind of investments you dive into and what your resources are to help you with that, but certainly entrepreneurship mindsets come into major play at some point along the way, if for no other reason to allow for expansion via leverage and all that you mention.

Still own and occupy the property, slowly adding value through renovations and upgrades including whole A/C upgrade, roofing repairs, and landscaping.

The thing I like most is you have 360 degrees of expansion so you can go north, south, east, west and find potentially something you like.

I enjoyed the book the E-Myth Revisited by Michael Gerber on how to think about business expansion. 

Go to a local investors meeting and ask for recommendations.As you gain experience, refine your lease to meet your needs.I could tell you that it's important to have a clause about tenant responsibilities with landscaping but you may not have a lawn or maybe you handle it yourself.

The landscapers I had to hire didn't do upkeep like that.

The cost of rehab will depend on your market and the price range.If you're in the Midwest, this is how I figure out quick repair costs based on pictures (keep in mind this works for the median price range of $100K to $250K) and if you intend to FLIP (fix-n-sell)- cosmetic improvements (paint, replace carpet with hardwood, new windows, landscaping) - $10,000- remodel (new kitchen, new bathrooms, appliances) - $25,000 to $30,000 (this will typically include cosmetics)- structurals (new driveway, new garage) + cosmetic + remodel - $40,000 to $50,000Since you intend to fix-n-rent, multiply the above numbers by 65%.

@John Bennett, The landscape of lending is always changing of course.