You can write off everything still, its actually better if flip takes more then a year as you can make it look like a long term capital gain, need a investor friendly CPA who isn't afraid to do what gets you the lowest tax payments. 

I’m also currently looking to upgrade to a software that allows me to transfer friends from PM to owner and will help me generate form 1099at the end of the year.

If your goal is personal-use real estate, cashing out the 403(b) is an option, but it will incur income tax and a 10% penalty, significantly reducing your available funds.

I have a friend with a skid steer, and if we can't do it it's probably not worth it!

I was a foster child who put myself through college on my own, and I have relied on some good friends for a place to stay as I grew up, which has motivated me to create a better life for myself.I have done a lot of research on real estate, and from my perspective, it seems as if wholesaling, which I feel my sales skills may help with, would be a good place to start to make some extra money to speed up the investing process.

Since your friend covers utilities, this offsets some of your cost.

And I hope to be ready to buy within 9 months (we are moving from LA)  Agents that aren't keeping deals to themselves (or friends) are a rarity.

Unless the contractor is a friend of yours, they aren't going to go to a house you aren't buying just to tell you how much something costs and if they did, it may not translate to the next home.

Still landlord friendly.

These loans are more flexible in some cases.As for banks in Cleveland, some of the more investor-friendly options to consider might include:Huntington National Bank - Offers business loans and could be open to working with foreign nationals investing through U.S. corporations.First National Bank - Another local option that has experience working with investors, especially through corporate entities.