I own a home and would like to brrrr it,  but i need advice on structuring the loan. 

If it hasn't been too long maybe it's worth try selling again.In terms of cash out refinance, most investors would do a 70-75% cash out refinance given it debt covers.

See if you can screen tenants more comprehensively and then offer them a long-term lease right off the bat.P.S.

Efficient negotiations secured the property for $158,000 on favorable terms.

Through efficient negotiations, we secured the property for $196,000 on favorable terms.

If you have $15K in student loan debt and are paying it off little by little (your words)-what are the interest rates, how long will it take you to pay it off, does it affect your ability to borrow for a mortgages (or save the down payment)? 

We primarily do short-term, but also do mid-term and long-term!

I will have capital gains at the long-term rate of 15% for my first and second interests acquired, calculated as the present value the condo will sell at, minus the stepped-up value at the time I acquired each interest.B.

There are a lot of variables involved so its hard to see unless you run the numbers especially since you might replace this home with 2-4 units and where the loans on those new properties would be at a higher rate.

@Michael Kaminski    There is no way around the requirement to move in within 60 days for a conventional loan and call it a primary residence to get the best rates.