Often times the smaller scale landlord/investor does not take into consideration certain liability exposures that could completely undermine their respective investments. 

And a soft remodel (paint, new vinyl laminate floor, etc) is usually in the 5-10 range for me...So you may have found a lucrative investment and an exercise program (especially if you become a small scale landlord)

Any patch product that works is so expensive that it's cheaper on a large scale project to just redo it.BTW it sound like the driveways in the neighborhood were improperly constructed.

Ideally scaling up my business in the order I previously mentioned.

When you treat it more as a partnership of helping each other it is much easier to scale, since your not wasting time arguing with tenants. 

Yes it makes it more manageable per house but it also makes it harder to scale up. 

I would recommend getting into the multifamily if you can, economies of scale are better.

I think a big fail here is that you do not get the value of the team, the economies of scale, the immediate hyper local knowledge to make your rentals a success in long term play, for cash flow with an eventual exit or reposition.Next, moving on! 

When you are small, if there is capital repair to made at the property, you don't have the comfort of scale of operation to spread the cost over a number of properties.  

Set up the teams and systems and you've got something you might want to scale.