This is very doable. 

Managing afar is def do-able but have a friend who is OCD stop by there once a month or every other month to get physical eyes and NOSE on it.

All four you'll have to drive off the 'hill' but if you are taking a day off from skiing they are totally doable in one day.

House hacking is doable practically anywhere you like.  

I've been working on a difficult deal, but I just know that it should be doable.

And refinancing into a long term with a bank is doable, but in today's lending conditions it can be tough if you don't have a great stable job, good income, and good credit.

Like Geof said it's definitely getting more difficult to get houses. 40k with $1,100 in rent is unrealistic but not that far off. 50k with $1,100 in rent is still tough but doable.

Yes the seller is mentioning lower expenses than this, but even with 50% maintenance cost it is still very profitable so I like to be conservative and make this assumption and if it ends up being less it will just be the cherry on the cake...Yes they are liveable (there is a brand new C of O so they have been inspected).Financing should be doable also I have not dig too much yet into this especially for the fact that it is a portfolio of properties.Your last question is one I've asked myself and to be honest no there is no discount but it is also much less time for me to spend looking and finding properties.

Something that is doable considering limited experience of such investor; offering a reasonable reward and manageable risk.For example I know Auctions have potentials for huge equity right at the time of purchase but there are complexities to them such as liens or deferred taxes.Multi-family units seem to be lucrative but then they have their own downsides.Flip needs experience in managing time, contractors …Which path is the ideal path to take as for the first deal?

It's still doable, and many buildings have been bought on those terms but you won't find as many sellers who will take you as seriously. here's how it would look on a contract:Purchase 2m1st: $1.5m (75%)2nd (vtb) $400k (@ 10% monthly interest only payments for five years with a balloon payment at the end, or whatever you can negotiate.