Will be difficult because you currently live in the property . is the 2nd unit livable and just looking to renovate ? 

Keep the current investment and buy another house hack to live in.

You'd need to show the income on your tax returns and/or have a lease and first month's rent/security deposit for the unit you were living in.

I moved to miami florida to study the economics and help apply it and it was a capital market as well. if you don't live in a capital market like Chicago, New York, Austin Texas, Los Angeles, San Francisco, california or miami florida I'd recommend moving to a market like that too. it will change your life. 

Did you read Lend to Live?

Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

It makes sense for house mates, spouses etc. to be Additional Insured on a renter's Insurance policy if they also live there and keep their stuff there (although I think anyone on the lease is typically covered anyway).

Tenants should be paying the owner.Do you also live in the house?

I would recommend that you start with buying a primary residence using a low down payment loan, like a 5% down conventional loan, live in it for a year or two and then keep it as a rental when you go and buy your next primary residence using another 5% down conventional loan.

Most of the “deals” have no meat left on bone except for maybe a long term rental hold after repairs.They ironically sponsor a lot of the meet ups I’ve been too here in DFW. of course they do they live and breath on newbies..