My partner and I have a couple projects going on at the moment in the Cleveland market, but currently don't have someone to take legit pictures or shoot video of the whole process (I like to have good before/afters to keep track of what we've done and attract investors). 

One is currently for sale and the inside seems to be in great shape via mls pictures, although the listing recently expired.

He has scholarships and federal unsubsidized loans that cover full tuition, fees and some room and board...but not all.Prob going to need around $20k for college.I have secured a $30k loan using the property for collateral to cover the college expenses.What would you do with the $30k?

See the pictures below.

I have been looking at a handful of potential deals and the majority of them barely cashflow or are negative if I include myself paying rent (in theory to cover the mortgage).

I own a rental property in Chicago that currently has a lease and the monthly rent covers the mortgage and HOA assessments exactly. 

Based on references, pictures and feedback of others; where does the quality of their work stand? 

You need to look at it like the business it is and maximize your profits.You mentioned at the end wanting to, “at least get the tenant to cover half your house payments.”

I rent out the spare bedrooms, which covers the mortgage, taxes, insurance, and repair reserve.

If you are relying on credit cards and anything goes wrong which is likely on a first deal, you will be stuck without reserves to cover expenses.