We've not met in person yet, but know each other.

I haven't personally dealt with any crazy insurance premiums such as the ones people have been advertising in like Tampa, FL.

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.

They seem to be a reputable company, but nothing beats personal testimonies!

I agree with Andrew’s comments particularly because this is a home you personally lived in and know intimately.

I personally think it is best to work with local professionals with a good track record. 

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.

Fast forward 2 years his landlord mentioned in passing he might sell the property; I was the first person on his mind.

There is a large population of low income persons who are poorly integrated and somewhat centralized.