The representative said the tenant would be re-evaluated after 6 months to see if they still qualified for the assistance and they couldn't guarantee a year long lease.At least with Section 8 its guaranteed money.

They are licensed brokers who make their money on the commission, I assume.

So chances of finding the right buyer, (DIY saving money type), with kitchen size/layout very similar yet flexible - willing to build/spec the cabinets around the size of the counters... is exceedingly slim.

I can put some money down, but I want to stay under $50k at absolute most and prefer to put down as little as possible.

It is about the time value of money.

My goal is for this house to be paid for over the long term, refinance to pull money out, and do it again in another nearby, yet different market (BRRR).

My biggest hesitation is tying up this much money in a property.

Unless you just need a place to park cash, I don't see how you ever make money on those. 

It is all about if it will helps the sale, in price or time it will sit on the market  which it ultimately comes down to money because of holding costs. 

Waste of money I think.