It seems as though you have developed a great strategy of handling these types of tenants, but with this being our first rental property (and me being a 5'1 female against these two), there's no way I could chance my safety. 

I know it's not ideal to start in this situation but in all honesty to some extent everyone in this industry does it. 

I want to get my hands dirty on this first one.... and ideally double-up every 18-24 months.

@Chris MacDonald  I am not a CPA but I am and have been a real estate professional for tax purposes for 40 plus years.. so I write every single trip off.. as I am always looking at new deals.when I was in Thailand last week I met with a condo developer who was offering 7% guaranteed rental returns.. on his condos went on a tour got the brochures and am considering that investment.. so that is a business trip. 

Even areas I likely won't work in anytime soon (large commercial developments, for example) still spike my interest. 

Of course ideally you get both in one property but that's tough to do unless its an off market deal or you predict the right area and get in early.

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They are discussing pre approved financing, package deals, fix and flip, and even development potential ! 

One landlord I know who keeps the water bill in his name has developed his own system that trains the tenant on how to read the water meter, and to take the reading to compute how much to include with the rent for the water bill; it gets close enough so that he has not fronted the water payment for a tenant who decides to skip town.If you have the tenant get the water bill where unpaid water bills become a lien, you will want to have some way of tracking that the tenant is paying the bill.