Have you looked at a little bigger multifamily, like in the 5-10 unit range?

I found someone local who is willing to handle property management (for 20%), but it feels like a waste if I'm already handling the listings and automation and integrations to run the business.

Does that sound like I am doing this right or should I just buy the property subject-to with maybe a one year balloon, then just bite the bullet and close on the property and once it's fixed up turn around and sell it again.

With that said, vigilance is still necessary to stay abreast of current and future legal changes likely to impact your estate plan.

I'd like to attend the next one. 

We would like to take out 90k of equity and the property if worth about 250k.

You saw a lot of that start to go away leading into the financial crisis, as more traditional retail banks started acting like investment banks, hence a lot of the regulations placed on them.And, as for "why not connect with HNW and family offices", most do.  

Big players like FedEx and St.

I'm not a handyman by any stretch but there are few things on that list that I'd like to tackle.

Many ideas sound like a great route to go down.