My first house hack/ selling my current single family home

[Ryan Hoffman-Scranton]

This coming year I will be taking my first step in the direction or real estate investing. I'm 27 years old and I purchased my first single family house at 25. After a few updates and repairs I plan to sell my house and buy a multi family home which I plan to occupy. I'm specifically looking for a 3-4 family home, which is very possible in my area (upstate NY) however, I am not opposed to the idea of a duplex if the price is right. 

   With the money I'm saving on a mortgage, which is currently almost $1000 a month as well as the profit I anticipate making on my house (after many updates and repairs) I plan to invest in my first flip. I currently work as a union carpenter and have been involved in the trades since I was 16 years old. I do not plan to hire any contractors to help with the flip. Any work that I don't feel comfortable performing on my own, such as electrical work and some more involved plumbing would be taken care of by friends and acquaintances who work in the field professionally.

  I will add that I do work full time and plan to do so full time until I get to a point where it just doesn't make sense any more. That being said I currently earn 65k-80k per year.

  Just looking for some advice/opinions from those who have been here before. Anything you would do differently? Where would you go next? Is a flip a good next move?  Thanks in advance!

[Matthew Reid]

@Ryan Hoffman-Scranton

Ryan, I am in a very similar boat. I have just finished my first deal on a duplex and have renters in them currently. Sweat Equity is all fine and dandy until you drag out a project a couple more months and lose on those opportunity costs and have to make the mortgage, and utilities every month. I did this on my second unit and ended up having to list it for rent later in the year and missed out on a potentially higher rent because of the not so prime time of year to be listing a home for rent. You may make less money by using a contractor but at least you'll wrap up the project much sooner and can get going on that next deal FAST!!! And on top of that if the numbers are so slim you can't use a contractor it might not be a good deal.