I think this is a calculation a lot of homeowners are making right now--especially if they have a low interest mortgage, equity, and their house will cashflow as a rental.The choice is a personal one of course, but I think your future self will thank you if you pull out some equity from your existing home with a HELOC for the downpayment on the next house and a cushion renting your current home, use a property manager as you have other things to do, and buy the next house and do the same thing again.

First person I hired, I also had them write their own job procedures and so on.

Appreciation is only a THEORY until a person SELLS, be it gain or loss. 

I had another person speak highly of New Western.

It has worked out for me, but I'm wondering if anyone else has another person they trust that I can float other, similar tasks to?  

Either way, $600 in cash flow should actually help your personal DTI if you go for conventional financing on a primary again. 

We recently started a Co-Hosting business and are managing for one other person.

I have my own leads (name of decedent, physical address of property, personal representative for the estate, Their physical address.

The cost to repair your vehicle, and perhaps the other person's car, will be WAY MORE than the cost of the insurance premiums you saved by not having insurance. 

What types of IRS/CPA approved payments are working well for rents to LLC entities to keep personal and business funds from co-mingling?