It had great views and was everything we ever wanted.  

For example, if the house has a crawlspace, I don’t usually recommend a duct scope because the inspector can view the ductwork under the house.

As a Realtor and investor, I have always recommended buyers included a letter to the seller describing why they are a perfect fit for that particular property. 

You described a classic case of Paralysis of Analysis. 

What are some ways that you all estimate rehab costs when viewing properties initially?

You probably need to view the property with a good contractor (or two) and get an estimate on each necessary repair.

So maybe you are being a little too aggressive...timeline goes like 1) prospective renter contacts you 2) you both set up a time to show/view house 3) if the prospective tenant is interested, then you send them your rental application.

If you want to buy multi-units one after the other you will need to make sure that they are turning a profit, otherwise banks will just view them as a liability

Please feel free to describe your experiences dealing with these loans as well. 

Having a garage, a mountain or harbor view, outbuildings with permits, any other particulars are adjusted up or down.