If you keep it as an investment property, a lot may depend on your location and condition.

I think it would give it a little bump in value but it all depends on the buyer.

Depending on the costs and a build to rent approach could work if you'd be willing to hold the properties as rentals. 

Depends.

.- Depending on your budget, do you want a small condo or larger residence?  

It depends on where you want to live, income, personality, and other factors.You could buy a large home and rent out the individual rooms to cover expenses, but this comes with problems.

My worry about per snowfall or per hr is dependability.

This $100,000 would be taxed at the applicable capital gains tax rate (0%–20% federally, depending on income) and subject to depreciation recapture at a maximum rate of 25%.

Depending on what you are trying to do, you may just have to do trial & error.

You'll be on call 24/7.This is a controversial statement but the average property manager who has proven systems in place can most likely manage around 80-100 properties on their own, maybe more or less depending on how many hours they want to work.