New furnace and possible AC, deck refacing, plumbing repair for one bathroom (ceiling leak), and 600sqft landscaping under the deck are the major updates needed.

The only major renovation projects for this property are a horribly done master bathroom remodel that will have to ripped out and re-done, the well needs some TLC, the exterior was painted or horrible color, and the landscaping was not cared for and thus all died (due to the well having problems). 

Growing job and population growth are generally strong indicators of future rent and occupancy expansion.

I think you'll like it here; the landscapes are very beautiful and we do have all the seasons here, too; although, we don't get too much snow.

We have a PM, but I also have built relationships with other professionals (landscaper, flooring guy, HVAC guy, painter, handman, etc.) in the area because I'm more comfortable with the vendors and contractors that I have had complete work on the house before.If doing everything yourself, I'd imagine that "how far is too far" is really only a function of your own tolerances. 

I own a townhouse in a community of about 40 townhouses...they typically have about $25-$30k in reserves, and that is more than sufficient...but they also are only paying for landscaping and snow removal with it.

From landscaping to plumbing and etc..

I know he has family that are in parallel businesses....a brother who is a landscaper, cousin who is an electrician, etc.

It's not cleaning the gutters and your ladder fell over or watering the landscape and the sidewalk got wet and someone tripped.   

Include everything from paint, new appliances, new flooring, landscaping, roof/gutters, need HVAC updated.