I'm thinking about moving my retirement savings from my current 401k into a self-directed IRA and using that to fund flips.Does anyone have a truly great accountant they work with?

But, in my defense, there was a disclaimer that I'm a note noob and wanted to understand the contingencies here. 

This is known as the self-sufficiency rule.

We both work full time and self manage, so more important right now to stay invested in that direction!

We seem to have similar goals since I'm also looking to start a property management company after I self manage my own investments for a little while.

The main reasons are:1)Most people, my self included, underestimate just how difficult it is for a small to find a good team on the ground in the location you want to invest.

If you have a business you can deduct expenses the are "ordinary and necessary" to run your business.When I was self employed in sales I deducted all of the things you mentioned.

My initial plan was to buy a pretty cheap terraced or maybe a semi detached if affordable near a university, with 4-5 bed-rooms and have one room for my self and rent the others out to university students.

Do you self host sites or do you use background services like Wordpress?

The reason you are reluctant to jump in is hardwired into you, self preservation, common sense, you actually recognize you're not ready to jump in with a good grasp of knowledge to risk your money.