I am looking for recommendations for managing Snow plowing & shoveling and lawn care across the portfolio. 

Brie, I decided to let the gym membership lapse and just pitch-in and shovel a little snow ... every second day it seems ;-)If you are motivated and a self-learner you can do absolutely fine without forking over the equivalent of a downpayment for courses.That said, some folks learn better when material is presented to them in a formal setting (i.e. classroom) ... if this is you, I would suggest auditing real estate courses at a local college or university ... no sales pressure, a more in-depth handling of topics and the tuition will be far less (better value for the money).

So we paint, clean, replace light fixtures and faucets,  shovel snow and do landscaping.We could afford to hire it out, but between finding and scheduling competent contractors, it is faster and easier to do it yourself.

@John WarrenOf the current tenants, I got 1 off Craig's List (Her credit score is higher than mine- never late, plants flowers, shovels the sidewalk, recycles everything so no trash, best tenant evah!!!)

If you have the lots and approved plans "shovel ready" then can you just sell them as pre-construction to-be-built?

For example, if you have a contract with the plow guy down the street to shovel your driveway each winter, this is generally personal in nature and will not be binding on the family you sell your home too. 

Next time get the dirt and entitle it but do not turn a shovel. 

My suggestions would be to find a broker who can market your house to surplus lines vendors as admitted companies in FL are probably charging you an arm and a leg.

As a concerned citizen I️ chased the mole down the street with a shovel.

The landlord gives the tenant a break on his rent for shoveling the driveway and sidewalk out front.