I would love to be able to bundle them into 1 loan, but have not found a lender who can loan on a single property under $100k, even when bundled with the other one. 

Making over a $140,000 isn't much of a horror story even if it's a "scary house." 

There were even some companies that refused to do business with them out of an abundance of caution.

And this doesn't even address the risks they take coming to this country, like the women and children that are sexually abused or trafficked, the men that are killed, the drugs that are hauled over, etc.2. 

While I will still lose money on it in the long run, I'm at least breaking even on it monthly and no longer have the headache of it. 

Primary goal for investing in real estate to grow my wealth (not to replace my W2 job).As the first investment, I want a safer investment with a goal to break even in 12 months and focus on learning & long-term cashflow/appreciation.

The attached chart shows a good example of why this is helpful.Bonus Depreciation - This allows you to accelerate the depreciation even further, deducting anything with a 15 year depreciation life or less in the first year. 

Perhaps I could help with some recommendations for other contractors to bid on the roof and foundation or even a new property manager.

Breaking Even & Potential Cash Flow•Your goal of breaking even in Year 1 is very achievable, especially with a 5% down payment and PMI removal via renovations.

The word arbitrage was not even being used then to my knowledge.