If the market flattens out, we can cash flow, if it continues to climb, we can benefit from more appreciation, and if it collapses and rents fall by 25% or so, we can survive with a little sweat and a hefty reserve and find ways to buy at the bottom.As always, your plan should allow you to win if the market keeps climbing, allow you to win if the market stays flat, and allow you to win if the market declines/collapses. 

I'm still fairly young at 31, so if I have put in some sweat equity and some extra effort and stress into getting a start and managing my own properties, I know I can still transition into more passive properties in the future.

Originally posted by @Fillipe Silvas:My boss at work......Helping him with this could be my way in to this worldI guess you've realized by now that your boss seems to have bad ideas in this arena & will probably not be the best person to partner up your sweat equity with.  

I do have some resources(Mainly the equity from my Primary Residence), skilled with Excel, analyzing date to make clearer pictures and sweat equity.

I'm not sure I'm reading the question correctly because I can't see any cons.As long as you can personally afford it since you'll be living in it, which the lender will ensure of course (that you can afford it), I think it's a great way to start out in real estate.As long as it's habitable (to your standards ;), you'll be able to really "get your hands dirty" with some repairs (even if hiring some out) but without the stress of having a tenant bothering you asking when the repairs are going to be done.Again, maybe I'm not understanding, but this seems like a great & classic "sweat equity" way to get started.

I bought a HUD, did the sweat equity thing and learned much, especially how others can do a much better job than I, in much less time.

Most of the repairs was all "sweat equity".

Keep in mind I'm a low maintenance type that just enjoys the freedom of walking out with my sweats and a T to work out and start my day. 

I know that sounds like a broad generalization, but without purchasing significantly below market value or putting in a decent amount of sweat equity, the property will not perform all that well and will hurt your debt to income ratio. 

So, I'd like to use some sweat equity (while I still can), and a HELOC to get something that can.