I believe setting the precedent upfront solves what could be serious issues before they even apply by giving them a rundown on some of the big key aspects of what the process looks like a head of time.Big indicators are verification of identity and verifying the references for documents when needed.

The ones I bailed out I actually took ownership of.. and got them out of hot water. there was no room for a loan but enough equity for me to step in and solve the issues.. 

I hope your problems get solved as soon as possible, best of luck!

The lender I spoke with in the new area said our DTI is the biggest issue, and that selling one of the properties would solve that problem, but selling one house hack for another of a similar price/cash flow isn't something I want to do.Still fairly new to REI so any and all advise is greatly appreciated.

You said your problem was solved, however, are you completely happy with the transaction(s) and do you understand everything they did?

Regardless, I'd get to those meetups and network- any of the problems you are having will be solved through networking with experienced investors. 

No clue, underwrite some deals and find out.https://www.affordablehousing.com/ is a website dedicated to section 8 rentals and may provide some insight as to what you can expect to get in your local market.

There are usually clues on the listing such as # of units listed vs the type of multi-family.

That solved the problems. 

The tenants complained about it, and I solved it by dropping a fence all the way down the property line and widening my side a little by having it repaved.