I was doing gardening work for him today and he mentioned that he wanted to pave grass in the backyard and plant scrubs in the front yard.

There are (2) 3 bed units, (4) 2 bed units and (3) 1 bed units.Rent ranges are as follows:1 bed units - $750-$1100   (used $850)2 bed units - $1000-$1500 (used $1000)3 bed units - $1200-$1800 (used $1200)A decent amount of improvements have been done over the years include (fairly recently) new roofs, city sewer and water upgrades, paving, 4 units have been renovated.Numbers/Analysis:Currently one unit is vacant and the rest of the units are substantially under market rents - 60-70% of market rents. 

Often grading comes in to play and costs for paving/driveway.

However, parking can be an big issue in a cul-de-sac unless there is enough paved parking area onsite. 

You could go to the city and file the paperwork yourself for the driveway and contract it out with a paving company to get around the upcharge for the General Contractor. 

Real property consists of land, buildings or other inherently permanent structures.Examples of Personal Property (contained in or attached to a structure/building)Interior LandscapingNeon or Other SignsDisplay Racks, Shelves or CabinetsWall CoveringsWindow TreatmentsCertain Air-conditioning EquipmentDecorative and Specific Business Activity Light FixturesCarpetingDecorative Trim & MillworkMachinery, Generators & Kitchen EquipmentAccordion Doors and PartitionsExamples of Real PropertyLand (non-depreciable)Buildings (27.5 or 39 year depreciation)Exterior Landscaping (15 year depreciation)Paved Parking Areas (15 year depreciation)Swimming Pools (15 year depreciation)Fences (15 year depreciation)Bridges (15 year depreciation)Side-walks (15 year depreciation)Docks (15 year depreciation)After the tax reform, the structural value of a building is depreciated over 27.5 to 39 years and the tangible portion of a building is allowed to be expensed immediately in the year the assets were placed into service by the business.

As I begin to pave my way to financial freedom, I have been met with the question of investing in a real estate deal first or focus solely on 401k and a ROTH IRA.

Roof: See if the assessor website shows when the roof was doneFurnace/AC: Could also be on the assessor website or check inspection tags or panels for manufactured datesSiding: Maintenance free vinyl is great for rental and sometimes needed for section 8 approvalwindows: if you have vinyl replacements that is a good signConcrete driveway: some areas required paved off-street surface for every possible rented bedroom. so see if you have the space.Foundation: any bowing walls.These are the biggest things I would check. if a place has any of these I would call a local contractor and see what he would charge to do any of these items and look to negotiate with those numbers in hand. 

That's going to be expensive paving.

Paving your way to financial freedom!