My risk tolerance is usually pretty decent, but given the stakes (of being unable to find alternative financing), I can’t seem to mentally let go of conventional lending options.The risks I anticipate are: 1) Credit score will drop with a lot of activity in a short time (though I don’t know how much), 2) The properties are pretty rural, so appraisals could be low or lenders may offer lower LTVs because of the rural classification, and 3) Sudden market shifts could make lenders skittish about vacation rentals, making it more difficult to secure non-conventional lending.My questions are: 1) How confident can I be that I will be able to secure a DSCR loan?  

How is land appraised to calculate the cost basis for depreciation?

The Government will not send an appraiser to your property to see if you have remodel it etc. 

With that being said, the appraiser will probably knock down the value of the property a little bit, and some renters will be reticent to be located next to a busy street, especially if they have children. 

With the rising house prices a person that waits closer to the 12 months could potentially receive a higher appraisal.

Other than that, you just need a credit score above 600 and the appraised rental income for the property must meet the projected mortgage payment.If your new business is the same line of work as your previous employment then you can possibly be qualified after 1 full year of self-employment.

The rented unit has some issues with the kitchen cabinets but is otherwise in decent shape, the cabinets are set to be replaced in a month or two.Comps in the area are higher than I expected, should I wait to order the appraisal till after all work is done?

Besides that you'd have to pay for an appraiser.

The bank didn't do a full appraisal, but instead used an online system called an AVM appraisal, and said my home is worth $198K. 

Property appraised for $146k last year (2020) in the As-Is condition of the lower unit not being livable.Status: Off-market property found through direct mail.Seller Motivation: He doesn't "have to sell" but would consider it for the right price.