If in your shoes, I would pay them to coach me on management skills specific to your state and market.

One thing I have seen over the years is the landlord or PM tells the tenant the property has to be paid for and the banks do not care about their situation.You go from a greedy landlord that is rich to being in the tenants shoes just trying to make a payment to get by and pay " the man ".Not the exact words but you are trying to portray that you have no control over the process and what happens next is automatic if they do not pay.

Just my opinion, but if I was in your shoes and I could somehow swing the nicer property, I'd go for that one.

If I were sitting in your shoes I would underwrite the rental increases at current CPI (or historical CPI rates) to ensure you're covered.

I hope to be in your shoes in the future, and feel I'll make it with hard work. 

Personally, In your shoes I'd just go the airbnb route.

For you category 1 folk, remember that you too were in my shoes at one time and that many, many others on BP are in those shoes. 

However, the owner uses, as the realtor put it, the old shoe box method of accounting.

Granted, this comes with its own challenges and demands, but if your biggest sticking point is your DTI, this is the most common sense way around it I would think.Another thing I might try, were I in your shoes, is to strike up conversations with local community banks or other portfolio lenders whose underwriting standards are different from a standard mortgage lender who is planning to sell your loan to Fannie or Freddie.Hope that all helps!

If I were in your shoes I would put 50% down on a 3-500k property somewhere and use this as a learning experience.