Two separate property appraisers (at the direction of the lender) were sent out to appraise, and neither was willing to appraise it as a "residence", and thus financing fell through (conventional primary loan).

I have had a couple of clients just get the loan approved with the long term rates and then the bank really doesn't care how they get it rented out after.

There's a reason that people try to buy properties off-market and that is because you can find sellers who care more about terms than maximizing returns.So start with a conversation: you already presumably have some rapport since it's your landlord and you've spoken before.

Financing: I’m planning to use conventional financing for this purchase.

Owner shouldn't care about your DTI.

They can get a better deal for there better care etc etc..

Sadly, FHA has a 2 year work history requirement, as does Conventional and USDA financing. 

Account Closed said, income and assets are the only "hassle" with a conventional loan.

Hey @Dalton Foote - I highly suggest  using a renovation loan and house hacking a multi-family if that is possible with your current life circumstances.The 203k and homestyle renovation loans are just amazing products and drastically help you reduce your risk, in my opinion, because you are able to leverage the cost of the entire renovation with such a low down payment loan.We work with a lot of clients who use these products in Chicago, and no matter what, in the long term, they gain great equity.If you aren't able to house hack - the process is essentially the same, but just with more money down with hard money or conventional construction loan.

Can you include all the lawn and yard care?