Condos and townhomes are typically less maintenance due to the fact the association will likely cover exterior maintenance, landscaping,etc.

Flooring, fixtures, added square footage ,updates, paint,trim, added washer and dryer ,carpet, landscape, walkways, drainage, plumbing, electrical What was the outcome?

Ask for a realistic estimation for site total cost, foundations, sitework, landscape, utilities. 

If you want to be outside of an HOA there are a ton of nice neighborhoods where you can rent on 30+ Day Seasonal terms.Based on what you described you may want to consider Palm River, I live there and it’s one of the first communities in Naples (1960’s) and has gorgeous established landscaping that you simply can’t find in newer communities.

Whether it's carpet, paint, flooring, landscaping/curb appeal having some ability to force appreciation is a good position to be in.

Our plan is to use the HELOC to convert our carport/pantry/laundry to a new master suite, do some landscaping, and then add a patio roof and a hot tub.

Reduce the amount of grass and add low maintenance plants such as decorative grasses with landscape fabric and mulch or native plants that don't require a lot of water. 

So I look for properties like the present one, and I would walk away from a property that exceeded the 1% rule but was located between Four Seasons Total Landscaping and the crematorium.I wonder what you look for to identify properties with strong inherent value.

Does anyone have any suggestions for landlord friendly landscaping companies?

@Mike Shulman - are you paying for any common area lighting, lawn care/landscaping, etc?