If I have found a "good deal/discount property" for 285K-300K that needs 15-20K of improvements.  

I find its kind of a progression.. you need a lot of capital for the note business the benefits of rentals is leverage of course.what i found was many did well as landlords then tired and just started to sell them off as they were retiring and note income worked for them.. and or they blended they had some rentals and had some notes. does not take a landlord that is suffering burnt out landlord syndrome but wants cash flow to understand how notes work.. but of course you have to choose wisely on the notes  for sure.. as it relates to BP  overwhelmingly the guys and gals on this site are going for bigger yields that they hope to make with NPN so they work for those.. and its not just passive income by any means its a business.. 

I've found that trust is one of the biggest factors that can make your loan process go smoothly.

I couldn't, but I found this if anyone is curious. 

Most buyer agents will bargain for repairs or reducing the purchase price / seller credits after defects are found.

Something you might consider is taking a look at your strength and weaknesses, I did that and partnered up with someone who brought those things I didn't have to the table. found a mentor,  And a carpenter,  I wasn't a Carpenter, so building things wasn't in my forte, I had a friend that was. 

I found a cash-flowing four-plex on the market for $250k.

As you probably found on your housing search many (possibly most) houses that are being sold for rental income have illegal units or rooms somewhere on the property.

I hope you found out at least how much the owner “thinks” they owe, and you have some idea of the value. 

We looked in Lowell/Worcester/Clinton too but found the same as you: riskier not being local to those markets, so it didn’t make sense for our first deal.