Some digging, gravel, and bags of asphalt would probably be fine.

Then saw cut the curb and put in a 2 car driveway , stone , asphalt or concrete depending on your budget 

For example:ROOF - Asphalt shingles should last 20-25 years.HVAC - I usually plan for a lifespan of 15-20 years, but your dollar amount looks accurate. 

I want to have more saved for just in case expenses for life/a potential rental property but also want real time experience and I think this would be a great way to do it.Your absolutely right that real "pounding the pavement" experience is the best way to gain knowledge and I think it is a reasonable request which someone can say yes or no..however I dont think contacting random people who are investors on LinkedIn or online is the correct way to do it.

(ours is up 3 miles of steep grade pavement and then another mile of gravel... but the view is to die for)I would urge you to be especially conservative with your vacancy rate - Maggie is pretty much dead all through the winter, and over the years I've seen many, many small businesses come and go because they couldn't make it through the low season.  3-4 months of little/no business is the entirety of your 33% vacancy. 

You benefit from their experience, and they benefit from you pounding the pavement to find the deal.

Expense are quite low: $2000 year taxes, $600 insurance, $700 street lights, $3000 vacancy/lost rent, $1000 upgrading UTL & gravel/pavement per year = $7,300/year expenses.

seller has all the leverage, and you've not built yourself enough exit strategies.start pounding pavement and talk to lenders to get out of this loan.

The roots are already lifting up the pavement and causing potential hazard, it is just a matter of time until it finds it way to the sewer line.

The key is just to hit the pavement, or find a local partner who will do it for you, to learn which parts of the Class B-to-C areas are good and which to stay away from, because some of these areas are block-to-block.