Just from 10000 feet it looks like your gain will be just about what it was from the sale of the first property minus the $3K of loss your taking on this sale.The convention is that holding periods are tacked together when determining tax status. 

Vehicle is paid of and through side hustles and and cashflow from the house hack to cover expense to have round an 80-90% savings rate.

Having lost $100K in my first round of OOS in the Phoenix market, I actually won't mind give it a 2nd try, but this time around, I would ONLY buy at pennies on the dollar...

I also keep hearing that it's important to get your feet wet and start, do you think it's worth investing in something that doesn't have as high a cash flow but is in an up and coming neighborhood?

I was very close to putting the fridge in the pantry (losing that space), gaining a couple of feet of counter and making up for the lost storage in cabinets.

You might work that angle to get some rehab money and allow you to work on the outside and then once that tenant moves out, do the first round of updates and move in. 

If one of them leaves or loses his job, the other tenant can typically hobble along until they can get back on their feet again.

I want to become an educated, well rounded wholesaler and investor.

If it were truly important, BP wouldn't round posts and votes on the left, which masks the information, and would also post the ratio explicitly.

Looking forward to searching out local deals and getting my feet wet finally.