He was also trying to say that if they DO accelerate, your losses are finite and minimal.

Once they provide the funding it is they who are at risk of loss not you.

If you are lacking any one of these three items, a bank won't work for you and you should use private money or hard money to get your deal.

Then the attorney says, well, he has caused you to incur a financial loss by devising this off the wall financing arrangement that is not common practice around here, we'll sue him for damages!

Second question- am I on the right track- move on, and leave this property be, if loss to lease, vacency, and submetering are the only value add plays, in a C class (not "hot and trendy") neighborhood?

The house had updates done and I am now budgeting for a new paved driveway, as well as large replacement items such as a roof that will be needed in about 6 years.

I built and sold 3 successful tech companies, was a CTO for two top US firms in DC as well, so let me play Devil's advocate — AppFolio and Buildium both offer reoccurring task/maintenance features for tracking such items like filters, law care, etc., however a simple operations change will fix all these issues.

I've spoken to my CPA and -- cutting to the chase and factoring in passive losses, etc -- if I were to 1031 it into different investments, I'd need to spend about $100K of equity against about $300K of debit (for a total of $400K) in order to qualify for a "like" property and avoid capital gains.What I'm looking for are thoughts on the best strategies moving forward. 

Hi @Kris Freeberg, A lot of people I communicate with get turned off from the price of Appfolio and the $12 million losses they make each year, and are worried what is going to happen to them when they run out of money.I bet a lot of others here would be curious about any other platforms you happened to look into as well.  

In the past, it wasn't worth dealing with an aggressive tenant, so I just waited it out (after experiencing enough loss of sleep).What you might consider is offering the tenant a portion of their security deposit back on the day they hand over the keys (if there's no damage) instead of making them wait, in exchange for cooperation in showing the unit.