Also I know that some lenders have an issue with making loans if there are more than 2 layers of roofing over the deck- this would make you have 2 layers if you do not remove the shingles.

You will need to get a local, rockstar Realtor, contractor, lender, and property manager.https://www.biggerpockets.com/blog/core-four-real-estate-tea...

Most lenders should be able to have both of these loan products.

Do the hours spent talking to an agent, contractor, lender to acquire the property count?

I wouldn't do a personal or private loan right out of the gate

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The roads are private.

Ultimately the lender will require a personal guarantee from the borrower unless the property qualifies for non recourse financing (which is rare and generally applies to larger transactions than those contemplated or executed upon by BP forum posters).

I can’t change the deed since it’s a private lender and we just closed last week.  

If you pay your contractors before work is complete then yes you are paying out of pocket hoping the lender agrees.