Getting analysis when starting out is pretty common, buying that first deal is a huge leap of faith. 

Quote from @Erick Pena: A "good" rental property is one that covers all expenses (mortgage, taxes, insurance, maintenance, property management fees, and any other costs) and still leave a surplus (commonly referred to as cash flow).Calculate cash flow as: Cash Flow = Rental Income − Operating Expenses − DebtThere's much more to it, but that's the basic idea.

A common misconception is that real estate properties under $1M have a smaller tax basis and therefore do not benefit from a cost segregation study due to the associated fees.

., longer-term, amortized, require escrow, commonly modified b/c of prepayments, etc.)? 

Basically common contract or agreement law.

There's a specific forum for House Hacking.You'll want to spend some time reading through there as it's a common topic.

This is a very common issue in parts of Milwaukee and I have done lots of basement reinforcing on our rentals.

I have heard that it is common practice that private money lenders collect a monthly fee thru various methods, I'm trying to determine what those methods are.   

Many Airbnb guests will want common utilities unless it is in a remote are where you go as a sot to sleep while hiking the area. 

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.