@Josh Humbert I’m also an over thinker and I ended up jumping into a less than ideal deal. I’m house hacking a duplex and it’s currently not cash flowing (yet) and there were SOO many unexpected issues. It will turn into a great deal once I do all of the forced appreciation I think it needs and am waiting for my appealed property taxes to be accepted. Once those two things happened I should be able to cash flow around 200-300 a month. Pulling from my own experience. If you’re going to pull the trigger on something less than ideal, at least try your best not to make assumptions about anything. Be as curious you naturally are about prior research but in the details of the deal and process of the improvements after you close.
That said, after I pulled the trigger on mine I realized how much more profitable it would have been to either have been more conservative with my numbers or to have waited longer and have found another deal. Waiting isn’t a bad thing and TRUST ME, the anxiety within analysis paralysis is nothing compared to the stress, anxiety, regret and anger of getting into a less than ideal situation and feeling stuck in your first deal.