What special purpose equipment do you have for an ADU/Office that required unique wiring for it to function? 

Figure out market rents, deduct expenses to determine NOI, deduct cashflow you want, plug remainder into mortgage calc at current interest rate, then add lender's required down payment.That is how much you offer!

Getting a good painter at a reasonable price requires persistence and comparison shopping.

Some, like ours, focus on offering optional services such as renters insurance or washer/dryer rentals without requiring tenants to opt into a full package.When choosing a property manager, I recommend asking about the structure and purpose of any fees.

I wouldn’t lower your credit score requirement or you’re going to end up needing to evict again and having turnover expenses.

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

A STR is a completely different animal in my opinion, in that it requires more work and much more compromise, but financially is worth the effort. 

The issue I had was that most lenders required a certain number of completed flips done under a LLC.

I think in this environment lenders are changing requirements, guidelines, and product availability daily.

Assuming you don't have a mortgage that requires a certain level of insurance, you can get a stop-loss policy covering all the properties.