The second company had a PM contract and due to other reasons we did not continue their services after a couple of months so tax stuff did not arise.

Quote from @Lamier Guzman: Quote from @Wale Lawal: @Lamier GuzmanWelcome to BP and thank you for your service!

We use a third party servicer to do all of this - much easier and when starting just tracked payments in wuickbooks as servicer tracked everything else 

However, he asked me to sign a one-year Exclusive Right to Represent agreement, as presented to him by his brokerage.His interpretation is that it applies only when he materially assists me, but I think the boilerplate brokerage language he was given reads much more broadly:"If during the term of this Agreement Buyer enters into a contract for the purchase of Property through the services or efforts of the Broker or Buyer’s Brokerage Firm, or by or through any other persons during the term of this Agreement" (emphasis mine).My concern is that, under my interpretation, if a fellow real estate investor wants to unload a property or if I get pointed to an opportunity by a former agent, colleague, or friend, this agreement could create an obstacle to moving forward with the deal.In the end, I didn’t sign.

You're running a business...you are not a social services provider. 

We have regular evictions at this scale and they typically will take a few months up to six or seven months if the tenant contest/hires an attorney.

If you plan to manage remotely, then find a good PM or have a trusted team that can inspect your property regularly - and be ready to pay them.

We don't allow any "deal-making" in the forums, which includes advertising your services or properties, looking for partners, etc.

Does he understand, Deeds, Due On Sale, Insurance, tax implications, servicing, contracts and so on?

Under IRS Publication 523 for 2023 dated February 2024, I qualify as "Service, Intelligence and Peace Corp Personnel" and for "qualified extended duty" (page 4& 5 - https://www.irs.gov/pub/irs-pdf/p523.pdf).