In a few months I’ll be living with family and paying $0 rent, which will boost my savings by over $2000 a month, though eventually I’ll want my own space - I’ll probably house hack, once I’ve picked an area I’d like to live in for a few years.What I’m not sure on is, how I should handle financing my first (and subsequent) property purchases.

Also, if i deduct the costs now as an investment and decide to convert it to my residence, are there any issues involved?

Would be signing up for a 5year hold and potential liability of a c Corp stock sale and any dirty laundry associated. https://www.noglaw.com/tax-benefits-converting-c-corporation-s-corporation/

I am setting up one side of my four bedroom house as a studio apartment with either one, or two rooms, and a kitchen (Converted laundry room).

I would either skip trace the auditor's list and call the owners to develop relationships with them and a deal will come down the pipeline eventually.

But that is mostly due to investors desiring to convert them into all residential units.

I mean eventually it would have to.

I am not a CPA, but I believe when a property converts from a primary residence to a rental home, that tax year you list the current value of the home and that becomes the new cost basis. 

Once graduation happens we will convert this to a rental (Air B&B or long-term).

If I buy a single family home with a conventional mortgage and 5% down, I'll have enough left over to eventually buy another property if owner occupy it and use an FHA loan.