Adding a 2nd story is tough on aesthetics very rarely do they turn out great. 

BRRRR strategy combined with house-hack strategy! 

Expect to put down 20-25%.Adding to @Whitney Hutten's comments, I underwrite to 15% combined for repairs and CapEx.Using a conservative rent of $995 as @Jeremy Pearson intimated, I bet you cash flow ~$200/month and see a CoC ROI of ~10%.

Brand yourself, get your own domain and brand yourself from the start (legally- you still need to list your broker).This is not a full list but this should keep you busy for a month or more and they are important but not urgent things all new Realtors should be doing but rarely do or they do it half A**.

I use 15% combined.

You can get more bang for your buck by combining house-hacking with the BRRRR strategy.Where to go from here:-Find an investor-friendly Realtor - check here - members -Get pre-approved for financing - your Realtor can recommend a lender or you can use the members tab to find someone in your market who has a reputation here on BP.

Combined, there are 22 beds and 8 bathrooms. 

To put the performance of these bonds into context, I feel performance is less FICO driven vs. a combination of skin in the game and experience as you alluded to. 

I get top ratings as a LL and get lots of referrals and rarely do I have an opening.  

I am an Illinois real estate attorney but I specialize in residential transactions.In residential purchases, title companies rarely hold Earnest Money.