At this time the primary goal is passive income and then scale within 5 years as I gain more experience and network. 

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?

This approach would allow me to learn with each deal and minimize initial risks.2️⃣ Go Straight to Multifamily: Instead of starting with SFHs, I could spend time learning the multifamily business and go directly for a 20+ unit building, maximizing scalability from the start.I have no experience with either strategy.If you were in my position, which strategy would you choose and why?

I tell people all the time: if you can't find a quality PM in a market, don't invest in that market!

Then what happens is the lender reports your payment history to the credit bureaus and each time hereafter if you ask for another loan and the lender pulls your credit then they are going to see your payment history and whether you made your loan payments or not which will likely influence whether or not they lend you money. 

The only thing we can think of is he deals with a lot of international trade and money and maybe it’s OFAC we just get a scripted message every time we talk to someone so we got lawyers involved. 

Every time Jim?

@Troy Parker Every time I have rented to a friend or acquaintance it has ended poorly.

Here's an ideal PM contract: The two keys are: The PM is incentivized to make you money, not charge high fees, and is contractually bound to provide reporting that you can understand in a timely manner. 

This ensures the landlord is notified any time the policy is changed, canceled, or renewed, making it easier to track without relying on the tenant.The difficult part is enforcement.