Once you get started it is hard to stop.  

I'll give my thoughtsThey couldn't really afford it because a through background check was not doneJob LossJob relocationEviction - they stopped paying because ...They need a bidder place due to new baby or family member that comes to live with themThey get put in jailThey need a cheaper placeThey want a shorter commute to workDivorceDeath (in family or one of tenants)You raised the rent too muchPerceived or actual problem with the houseHigh Utilities at your house

If you have $20k from some "gig economy" side hustle that can't be used as income at $20k/12=$1,666/mo, it can still be used as an additional $20k down, meaning you need to borrow less, meaning you can take the same income that can be used further.... it takes less income to borrow $80k than it does to borrow $100k!

It’s never stopped a transaction but it’s a definite headache and head-scratcher not knowing when these arbitrary guidelines apply.  

The margin for error is just to slim when you are borrowing at negative leverage.I would love to attend one of @Jeff Greenberg's meet ups and will try to fit it into my schedule. 

Most of the time a 5-10 year amortization the property will not cash flow after debt unless the loan to value is sufficiently low, which most borrowers are not looking for.

It might be hard to get a lender to borrow on a property like that unless you have a strong partner with a history of doing similar projects as the lead.I'm not sure which investors you have been speaking with that are not very excited to buy, but it likely relates to the strong real estate market and the fact that there are not as many deals around at this time. 

Also, it's sort of within walking distance to metro stops.

They can also be used to borrow from.  

Would it be advantageous for loan qualification purposes to become a co-borrower on a mortgage with my LLC (as opposed to a guarantor)?