House hacking is very popular in the DC area.

I am just getting started learning how to analyze deals, but in my initial research, it looks like getting positive cash flow in my neck of the woods is going to be difficult. 

I probably won't be buying anything for another 2-4 years, so right now I just want to learn how to analyze deals at least to the point where I can tell if something is obviously not a good deal without spending a lot of time crunching numbers.

It's all losing large amounts of money to be popular.

This is popular in Philly.Download BP’s newest book here some good due diligence in Chapter 10.

I'd read books on analyzing the numbers for buy and hold rentals. 

I need to get this down so I can analyze any wholesale, flip, or buy and hold deals I come across.What approach do I take?

Your time here will be well spent.Your profile is empty and there is no mention of a specific REI area of interest, so, I added the below links from three of the most popular niches for your selection of one or all.https://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/ (Ultimate beginners guide to wholesaling)http://www.biggerpockets.com/renewsblog/2014/01/07/flipping-houses/ (step by step guide to flips) http://www.biggerpockets.com/renewsblog/2013/02/22/buying-rental-property/ (how to buy a rental property)Now that you have made the move, below are some links that will help with the navigation of the site. http://www.biggerpockets.com/startherehttp://www.biggerpockets.com/meethttps://www.biggerpockets.com/alertsHow to Use @Mentions on BiggerPocketshttps://www.biggerpockets.com/ruleshttps://www.biggerpockets.com/termshttps://www.biggerpockets.com/inviteshttps://www.biggerpockets.com/perkshttps://www.biggerpockets.com/forums/categorieshttps://www.biggerpockets.com/courses/a-beginners-introduction-to-real-estate-investing (video courses)https://www.biggerpockets.com/real-estate-investing (Ultimate beginner's guide to REI)Before your 1st purchase, please ensure you visit the below link for some tips.https://www.biggerpockets.com/renewsblog/2014/12/19/real-estate-investing-success-smart-tips/REI books suggested by BPershttps://www.biggerpockets.com/renewsblog/2015/11/13/7-real-estate-books-beginner-investors/(7 absolute must read books for beginner REIs)http://www.biggerpockets.com/renewsblog/2013/04/14/best-real-estate-books/?

I'm a little worried that I will be hit with a giant tax bill at sale given this area (Durham, NC) is rapidly increasing in popularity and thus cost.   

I have known that Memphis is a good place for high cap rates ROI etc and a popular rental market with investors but was trying to focus on markets that had noticeably strong economic outlooks.