The issue is this negative initial cash flow increases the amount invested which will impact ROI forever.I do not do flips, but if I purchased this property I would be flipping it rather than suffering that level of monthly negative cash flow on that cheap a property.Regardless if you rent or sell, add a closet to each bedroom.  

Madison (senior living) and Nelson (student housing) have suffered from a combination of poor planning and poor execution, as our income from those investments has either stopped or diminished.

We both agreed.Tenant argument to me has always been, they are unable to pay rent due to PTSD suffered when they had several relatives die. 

Let me ask you this way.When was the last time you planted your butt next to the mail box when you got bitten by a rattlesnake hoping some doctor would send you a mailer on what to do when you get bitten by a rattlesnake?

can't" usually means there's something they don't know or is not being creative enough, I'll plant a seed that I received from my CPA that I won't butcher because I'm not a CPA.

We went way over our expected budget - by far our worse budget miss ever (remarkably we were only 0.5 week over our 2 month timeline).Using my rule, take the estimates and double them then add for lost occupancy and that is what I would be seeking or the owner have the work done using licensed contractors and do the work, take the risks, and suffer the vacancy costs.If you purchase having to do the work and your appraisal can handle it, the credit at closing is superior to price discount.  

How would you approach the seller to plant the idea of seller financing.

Think of it like planting two trees instead of one...they might not bear a ton of fruit right away, but over time, you'll have a richer harvest.

I expanded fast and my reserves for sure suffered temporarily ( was taking some reserves for future downpayments) , but am aggressively building those back up, while growing my personal savings bucket, and do very strigegent tenant background checks and references.   

They can do some repair to an old roof, then apply a plant based spray to the entire roof to replace the oils in the shingles that the sun has baked out over time.