Experience depends on who you deal with - the cleaner the loan file and more organized your paperwork the smoother the process with any private lender.

Is the loan assumable? 

Somewhere in the middle is likely your best bet for a 20 year timeline.I have almost 50 units here myself and that's about what my portfolio is cash flowing at this point combined LTV is around 65% as loans have gotten paid down and values have went up.

As of today I own 13 doors; 3 of them UD student rentals and the rest in Wilmington.

@James JeffersonHi James,To buy out the property you need to probably apply for a loan through any lender.  

Pay Down the Loan Faster:I’m considering applying $40,000 annually to the loan principal.

You can buy a rental house, put $60,000 down and you will have to get a non-recourse loan for the rest of the mortgage.

Based on the numbers seems like it was a straight forward conventional loan...any challenges?

Should we pursue a "cheap" rental in order to build rental history in the hopes of securing DSCR loans down the road? 

They then missed out on several more years of growth because they got out of the game and waited on the sidelines for things to look better. 2010 to 2012 was the period that cash investors were the players or those with IRA keep in mind investor loans were still basically non existent in those years for all those expect very well to do Investors beginners were not getting investor loans.