I want to share my most recent deal because I believe it is a true testament to how the small wins and knowledge gained compound over time, resulting in the hockey stick of exponential growth.Back in April of this year, I purchased a 5-unit commercial property after only investing in small multi-family properties prior to this.

Those are typically meant for larger projects and with well versed Contractors.

So in your examples the first option would be commensurate with what we typically expect if I am understanding correctly.  

I read this as a first time landlord and it helped me gain a ton of confidence and also taught me what I can and cannot do.

Preferably, not already operating as an STR so that you can gain the value you add by creating it. 

After sale costs this would net me $175k+ as I'll be able to take advantage of the capital gains exclusion.

Most condo owners I know then just have a typical walls-in policy to cover the interior of their unit (that's would your homeowners insurance you mentioned).

When applying for a DSCR loan, lenders typically assess the property's income-generating potential and calculate the DSCR to determine the borrower's creditworthiness.

The session typically takes about an hour.

Being a private money lender who lends out my own money, the typical response I receive from potential borrowers is that it is hard money.