There are 2 main ways to cover thees costs: 1.

That said, with $75k you’d need to make about 9% cash return each year to cover your student loans.

My goal is to build up enough cash flow to cover the gap between the time I decide to hang it up until I can access my retirement funds.

After waiting for several months, I purchased a 2 bed / 2 bath condo in Fremont, CA for some ridiculous price at the time and with a mortgage that I could not afford and rented a room to various co-workers to cover about 50% of the mortgage. 

It needs a heavy rehab though.

Calculate your bottom line using 70% of ARV (After Repair Value).Do not spend more than (.7*ARV)-RC (Repair Costs)Example: House is appraised at $100,000 *if repairs are made*...7*100k = 70k.Repair costs are expected to be $25k. 70k-25k = $45,000 (DO NOT BUY THE HOUSE IF IT IS OVER $45k)Take another look at the ‘going rate’ of rent in your area, make sure your cash flow is enough to cover ALL costs and include a buffer for taxes and unexpected repairs.Look at the property yourself - try to eliminate assumptions.Have a trusted professional assess and confirm info about repairs that may have been overlooked.Look at how much work you can do on your own and compare it with contractor rates to complete all repairs.

I plan to have 2 roommates, which will cover the expenses and then some. 

If US Bank is getting paid and the amount of equity in the property covers the 1st and 2nd at a foreclosure sale then the second is less likely to deal.

My income fluctuates do to my freelance work.I have an amazing credit score 799I tried to get a line of credit and got rejected from my bank.I now have an offer to refinance and get cash out for a total of $375K loan at 4.5% for 30 years (That gives me a bit more then $175K out)My plan was to keep my mortgage as is rent my place out to cover it and get a new multi unit to live in and rent.

You could try to meet halfway with the price but another tactic is to offer to cover closing costs.