What to do?? Nervous to purchases another house

[Michael Taylor]

A house is asking $300,000. I got a quote that I could make $55,000+ from short term rentals from a property management company in the area. I asked for a disclosure sheet and very little information was discovered and some things contradicted each other. For example they said no pests, but selected no testing had been done, they didn't know how old the septic tank was, when it was last pumped, or the frequency, and didn't know age of roof. They purchased it back in 2020 and are already selling it. I found old photos and they did some work to the interior. 

I ran the numbers and came up with an offer price. Of course they can either say no or accept my offer, but is it worth waiving the inspection and offering asking to make $55,000+ per year not knowing full extent of damage they decided to turn the other cheek at during their own renovation?

Background: I purchased a place at asking in May, waiving inspection believing it was "turnkey" based on buyer agent and pictures. Got inspection day after closing and came up decent no big issues. But all the problems came out bigger than what the inspector suggested and I've dumped a lot of money into this terrible house. So even purchasing this current price with an inspection contingency makes me nervous because the inspector could miss things and i can get screwed again!

I'm nervous to purchase another property because my first one didn't turn out so great. What should I do?? 

Thanks for the help in advance!