Before that I was a real estate agent for a short period, so I have an understanding of the market and researching properties.

This is a very valuable skillset to have in your arsenal as an investor that can dramatically increase your net worth in a short period of time if the strategy is applied correctly.  

@Eric Smith A 1031 exchange with a related party is possible but comes with strict IRS scrutiny and holding period requirements.

So you are better off finding someone who wants to rean interest on their money and getting a promissory note signed and giving them a 10% interest rate and having them give you a 15k loan interés only for a 12-24 month period.

@Jeff Nash, noted the two year period. 

@Ryan Kelly mentions what is known as extended dwelling coverage.  

So even if you miss a month of the higher rent, it will kick in after you satisfy the appropriate "notice period" or they of course have the option to terminate and leave.

First tenant was on a fixed income as a retiree, so I was hesitant to increase the rent after the first lease period.

Even better, I might be able to snag it well under market value since it's an estate sale that's been sitting on the market for nearly 200 days.Here’s the challenge: while I could afford to purchase the property under market value, I’d be stretching my budget thin to cover the mortgage during the period I’d be remodeling the basement to make it rentable.

A truly "motivated" seller tends to not really care the amount of earnest money and you could also structure your EM due at end of your inspection period.