Lenders like b of A used to approve mortgages to those filed bankruptcy previously and they turned out to be reliable borrowers.

I am planning for both scenarios. but what will help me sleep at night know that if I had to move out of a house hack, my unit would cover the mortgage (plus more).

Your mortgage will be close to $1150, plus taxes (~400), plus wear and tear (assuming a new house, lets say 10% of rent = $180) ,and plus (potentially) a property manager (~10% of rent = 180).

However, house hacking is not about cashflow, it's about of setting your mortgage and not paying rent, with the added benefit of future returns, which is why if you have the capacity to do one a year, it gets multiplicatively good. 

I do want to mention that I am using a 2nd home mortgage product which is a bit better than an investment property.

Some considerations:- The least expensive route is to have a bookkeeper and a tax person separately, since bookkeeping is generally cheaper.

I have 9 rental properties and pay a tax attorney $800 per year to prepare the taxes, but every year it seems that I find a few mistakes like mortgage interest not deducted on one property and insurance not deducted on another.I had assumed that for $800, someone was spending 4 hours entering my information and going through things to make sure I was getting all the deductions I was entitled to as well as preparing things so as to minimize the chances of an audit. 

I've had termites, sweating slabs with no plumbing leaks, broken drain pipes, missing HVAC units, copper stolen from under vacant property, properties red tagged by the county, accelerated mortgages because of due on sale clauses, pets that did 35K of damage, and so many other things. 

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

got a 4 unit building for sell in the north suburbs of chicago that cost 25k over apprised value but seller said they are will to hold the financing with 100k down. rents out for just over market rates leaving a noi of around 30k. so my question is, even tho he's over market and appraised value, but willing to hold the balance of mortgage, is this deal worth it?