We had the loan estimate in hand but decided it was too big of a PIA to make it worth it.

.- she sounds like a PIA.  

The only people who read the lease are the crazy parents who redline items and send it back thinking we now want to rent to them after being such a PIA.

I know my local office is a PIA to deal with, but it could just be something similar across the board. 

Another good thing (which is also a PIA) is that the borough has strict rental guidelines and also strict CO policies when properties are sold or rented.

- If so, 1031 into something bigger and easier to manage and then when you pass, the inheritor receives your property(s) at a stepped up basis - subject to Inheritance Tax limits.Otherwise, sell one every 1-5 years when you need the cash, so you can plan expenses to offset capital gains.14 properties - presume these had to have been single families.Oh, I'm modifying the original post to mention leaning toward creating a trust which we manage..so we would own very little yet manage the trust which owned investments and such.Here is what I understand/misunderstand (better or worse) on moving every 2 years (as we are open to that albeit pia.) • Multi-unit would only support a %, so a quad would 25% and prorated over all years of ownership....witteling advantage to not worth the effort. • Single unit properties get pro-rated.

You've signed up for one PIA if the owner is still in the house.One way to tippie toe into this is to hook up with short sale agents and start working with them offering to door knock the NOD folks. 

That said, VRBO doesn't do auto messaging and that's a PIA that makes a channel manager a nice tool to have, but often the cost isn't worth it until you get at least 1 more unit - again, my opinion.  

This is my smallest property but the biggest PIA to get lending on since I can't shop it to Fannie/Freddie and competitors.

Dealing with commercial financing is such a PIA compared to a single family home.