I know that I would need a landscaper, maintenance crew, property manager/assistant(?)

You should try to learn everything you can about the property.You can search on here and find great due diligence checklists but the most important in my opinion to understand are A) the majors systems/capex items, roof, hvac, plumbing, electrical, foundation B) The current tenants and what their plans are C) the operating expenses at the property particularly utilities but also miscellaneous stuff like trash and landscaping.

But as far as snow or landscape I planned on doing it myself since I will be living there.

We really don't have any off season except for things like landscape and pools and then that is only a few months if any. 

Much more than I expected, but I priced it out with fence company, handyman, landscapers, and GC ... all were between $14-$18/lf.Labor's in short supply... prices are high.Glad to split with neighbors

HOA fees are a downside but can save you labor and time on landscaping, roofing, outside work etc.

It will need some landscaping work, some trim inside, new siding possibly and some deck work such as painting and adding some wood, structurally the deck is okay.

They will have a small amount of landscaping equipment on the property. 

It needs a new roof, new windows and doors, interior and exterior paint, floors need to be buffed or refinished, new refrigerator, new flooring in the bathrooms as well as new fixtures, new lighting fixtures throughout the house, needs some patch work on some the downstairs ceilings, and some landscaping on the outside of the house.

If you grew up in construction, trades, landscaping, etc the answer would be different than if your in law or medical school or have " handy " back ground