This is how I see it:Single-Family Homes:Pros:Larger pool of potential tenants (families).Simpler management (one tenant, one lease).Often easier to finance.May appreciate faster in some markets.Cons:Only one income stream.Vacancy hits harder financially.Duplexes:Pros:Two potential income streams.Live in one unit and rent the other (house hacking!)

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 

An easier route would be to convince him to go in on the short term rental together in a partnership. 

I find condos/townhomes to be easier to manage out of state because the HOA handles a lot of the maintenance, just be aware of condo fees and find a place that is reasonable like $300-400/mo or less if you are lucky.

Happy to discuss further on a call if that would be easier for you. 

Absolutely.If a landlord is listed as additional insured (rather than additional interest) they cannot make a claim against one another's liability policy for damages - it could completely jeopardize the coverage they think they're making it easier to get. 

I am guessing they probably raised $15-25M from investors for the deal, so while the bank would still be covered investors would appear to collect maybe 10-20 cents on the dollar if they were to liquidate.if that's the case then I don't see buying one year really does anything unless I am missing something ? 

The sooner you use a system like this, the easier it will be to keep track of it all when you have multiple properties. 

It wasnt an easy decision, but he’s now breathing easier with stronger cash reserves.Another thought: refinancing.

I understand they can make our life a lot easier but is it worth it if it eats up a lot of our cash flow?