.: I just got billed $365 by my property manager for replacing a toilet fill valve and supply line.

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

Quote from @Michael Smythe: Besides MANY self-labeled "gurus" exaggerating their success, many of them just supply readily available info.If you're too busy to find the info and are willing to pay for it, no problem as you accept their time vs money solution.REGARDING S8 GURU ISSUES SPECIFICALLYMost of them don't share all the facts about how Section 8 actually works.They claim you can get HIGHER rent from S8 tenants vs private-paying tenants.Why would the government allow our tax dollars to be spent this way?

Fears/risks: the underwriting projection seems too good which likely means very aggressive.  

Basically, the demand is much weaker than the supply. 

Here’s how it works:Population Decline or Stagnation: If the population is static or shrinking, the current housing supply meets demand, and property prices decline (in inflation-adjusted dollars).

It seems like the court was quite aggressive on some of those notes.

So Supply and demand have really shifted quickly. 

A new owner with more capital can easily come in and decrease vacancy rates and increase supply to realize a 2-3x revenue.

Also, it seems that you took on a very aggressive path to reaching your goals in such a commendable time.