And some of the biggest repairs not for some time (roof 20, hvac 10, etc) .To me, building a new sfh should allow you to get a bigger discount than what is typically available these days unless you're really getting lucky. 

How will you pay for a new fridge or roof?

The real problem comes in when the unexpected happens, like a roof repair, or a boiler replacement, on top of the negative cash flow.If it was me, I would try to save more, take out less debt, to help with cash flow.

Additionally, I’ve deepened my understanding of real estate terminology and gained valuable insights into the critical aspects of properties, from structural components to factors to look out for. 

Also, I’m curious—have you found that lenders’ confidence grows after seeing how smoothly things run, or are there certain aspects of the deal where they tend to focus their due diligence?

The major concerns to me are the roof, the hot water heater, and similar.  

I get the depreciation aspects. 

Why not just write the initial $50k offer in the name of your company and avoid the wholesale aspect of it altogether?

So long story short we have a traveling nurse staying at our rental that got some water damage when the roof was being replaced, they don't have renter's insurance (which we require in the renter's agreement they sign), water damage has been remedied and is cosmetically minimally affected and still very much in a liveable state.

Still making mistakes and learning.Sometimes you have to tear the roof off the old structure and build new.