In theory, assuming there is a MASSIVE amount of trust, including trusting in this fellow not trashing his DTI any more, you could allow him to be put on title with you for six months, and then he could possibly do a debt consolidation cash out refinance.

We currently have two management companies covering our rental properties and we are thinking of consolidating all into only one of them and halting business with the other, but are not sure the best way to do this.

There shouldn't be any technology constraint here.However, I am not surprise that Propertyware won't let you do that ... their client is the property managers and it's in their incentive to not allow you to consolidate your portfolio and own any of the data.

I work at Kohl's Floorcovering in Cedarburg and if you would ever need consolidation on your flooring let me know. 

The way around this is consolidating insurance policies and purchasing a larger umbrella policy.

My plan is to ask if he'll consolidate my debt in a loan on a HELOC, letting my credit recover and house hacking with family after I move out in April 2019.

Bank will need to see a consolidated Income Statement to make sure the DSCR is enough.

If that LTV's still too low, I'd give up on the HELOC option.If I were you, I would first try exhausting balance transfer options for Unsecured revolving at 0% APR, and if that fizzles out, Sofi or equivalent could lower that rate drastically on an unsecured consolidation.

Let them know what you are doing and shop for the services that will allow you to have a certain amount of administrative consolidation (such as shared logins and dashboards) while also maintaining truly separate accounts.Discussing your strategy with an expert in tax or asset protection is a good idea. 

I'm familiar with Green River, Main Street, Carrington, Equator, Goodman Dean, Clear Capital, LRES, Inside Valuation but thought there might be some name changes, consolidations or start ups.