Increasing bathrooms, refinishing whole house woodwork, updating all mechanical items, and adding those modern touches throughout.

Look and place an ad on Craigslist and Angieslist.

I have two options in front of me either to obtain a rehab loan, which will cost me $10k for six months ( points, fees, interest) or just finance the entire deal with my own money (cash).The rehab loan will enable me to obtain an additional property, so in six months i'll have two properties ( one with the loan, another with my cash)  but it'll cost me an extra $10k (on top of the regular down-payment which in any case i'll have to lay out) .

Depending on the duration of your tenant, you can calculate the amount of extra money needed to set aside for this expense.

From about February 2018 we decided things were getting serious and I spent enough time at her house that I might as well put my home on Airbnb to make a little extra income since we spend enough time at each others homes (currently we have made about $10k off of my home on Airbnb). 

I added the numbers up you are better off buying a clean title in good condition property.31K+19K+7K+closing cost, negotiator fee I got close to 60K...… If it was me I pass.

Either way there is a refinance so you would be looking at doing an extra loan.

Not really looking for a $700k house but something small to start out with, maybe some extra cash to play around with in the future and a little bit of passive income as I study.

Some of the larger expenses-Interior/Exterior Paint, Storm shutters for a few of the front large windows, added additional cabinets to one unit, New refrigerator from Dent/Scratch store after old one died, Laundry units that tenant pays +$50/mo for etc.

But in C-D ( is there a D?