I know a few more people who's purchasing with him, from what I hear, every single closing was delayed due to supply shortages or other reason. 

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?

The Wichita market currently does not have enough supply to meet the buyers need. 

https://www.har.com/content/department/mlsHouston Real Estate Highlights in November, 2024:-Single-family home sales increased 6.0 percent year-over-year;-Days on Market (DOM) for single-family homes went from 48 to 52 days;-Total property sales were up 3.3 percent with 7,750 units sold;-Total dollar volume rose 11.1 percent to $3.1 billion;-The single-family median price was up 1.5 percent to $329,900;-The single-family average price climbed 4.1 percent to $418,903; -Single-family home months of inventory registered a 4.4-months supply, up from 3.5 months last November.

So Supply and demand have really shifted quickly. 

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. 

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

If you do outsource, some management companies will cover various things like cleaning, supplies, etc. so look into that as well. 

Do you think supply with surpass demand?

Hope this is helpful as Texas markets are sometimes not that easy to navigate when it comes to long term rental due to high property taxes and an overwhelming amount of supply on the market.