Is the fact that a wholesaler, isn't as willing to give some sort of information on a lending company or particular investor a red flag?

Are there any other red flags or even better, what words or descriptions peak your interest when looking at potential properties.  

The property also has some very obvious deferred maintenance that an appraiser is going to flag; I suspect someone would have to pay for repairs in order for it to qualify for financing, but I haven’t had a lender drive by it.

It can definitely be done, don't be discouraged, but don't be too excited that you aren't open to the possible red flags...

If you complete and sell the home in four months you will pay over 30% APR for this loan.Another red flag on your deal is how you're calculating your  after repair value.

Like an 2.5 etc.If you are in the range of market rents, I think having an adjustment to market rates is probably not unconscionable should that person stay on.The seller being tight lipped about the renter could be a red a flag or maybe not.

Red flags abound. 

Are these red flags?

I hope it works out, but I'm surprised no one highlighted your bankruptcy as a red flag to getting a loan...unless your step dad is helping you out on your first couple, and you're able to save enough to buy more houses in cash. 

Elevator sounds like a red flag , is that just for you're units or you are offering on 2 condos one on top of another in a larger building?