Not sure what state you are in but Red Rabbit insurance is amazing.

@Erin Garcia I am currently working on 2 multi family projects myself in the Avondale and Logan Square areas and have worked on a few deals on the southside.

It was under contract but buyer ended up losing her approval with the lender so now I'm back to square one.

IMO some of your numbers seem close, but at these small purchase points, being off by a couple hundred bucks can make the difference between somewhat profitable and in the red.

State that you feel the work is 50% complete and you’ve paid him $$ or 50% of the total, so you’re square.

What sort of red flags are here?

7 weeks after purchase we will have 3 parcels, one with a 1 bed/1.5 bath garage unit renting for $650/month, another with a 2,200 square foot farmhouse renting at $1,250/month, and the third parcel is an empty lot.

Please have your buyers agent calculate sold comps Price per square foot in The Farm at Wescott.  

We are mid conversion on a 45,000 square foot conversion. 

It means nothing.Pay $5,000 to "Open the Door" and you have bought a black box of whatever the seller wants to provide (a paper application handed to you from a lender, a website address, etc...)When buying something like this and "Sales Fluff" is introduced into the conversation (vs. hard facts such as, a line of credit will be set up for $X 90 days after doing Y with Z lender, etc...) there is unusually a reason for the "Sales fluff".Ask for a copy of the contract and take the time to read it to see what you would actually get for your $5,000, and if the contract has "Sales fluff" in it--Buyer Beware.If there is no contract, or they balk at giving you an opportunity to read it (pressure you into signing now), it might not be such a good deal for you.And Sales fluff may be a red flag about other parts of the "Opportunity" also.Good Luck!