I have been tinkering SquadHelp for a bit, I added several domains, got some premium approved but they seem to drop the prices a lot.

I think the incentives are flawed and can work against the domain owner/seller. The thing is that SH is a business with a lot of constant costs both operating and marketing. They are targeting on getting the majority of revenue from a lot of mid-ish priced domains.

It might be that a domain investor is aligned with that mentality of lots of small-mid-sized domains, frequent sales etc. but it breaks down on long-term investors with a different mentality (betting on the growth of a industry or rare 1 word domains that might happen to sell in 5 years).

So this is one, the low prices for mass sales mentality. Not letting the seller control the price and instead constraining them on the scale.

The other annoying thing is the inflexible "flexible payment plans", where you might sell a $10k domain that will be paid over 3 years and there's no control to reduce that period. Either you can't offer flexible payment plans or they control the timeframe.
$10k at 3 years with the inflation going rampant is even more annoying. $10k but you get less than $300 per month and contentiously losing profits every year.