Although I partially understand the skepticism about your PM possibly trying to scam you, it seems a bit odd to go straight to distrust, if this is your first repair issue.  

Seems like it should be pretty straight forward for most insurance companies. 

Hopefully one day I'll be big enough to need an accountant to keep it all straight. :) 

The burden shifts to you to be the straight shooter. 

@Sean Ramuchak Lots to unpack here so I'll try to get straight to the point.

How do the returns differ versus the straight 'owning rentals' game?  

depends on your strategy and resourcesif you are looking at NQLA's (nonqualified loan assumptions) to rentalsor straight conv purchase rentalsor BRRRRRRRRR the locations may differ

Between that and saving I can have about $200K cash in less than 3 years, it would just be difficult to buy another property during that time, I would just have to get creative.Pro - quick equity buildingcon - no additional cashflowScenario 2 - Out of state This route is a little more straight forward but I would look to find a market, which I have already done a good amount of research, and start off with a single property, shoot for $200 + cash flow and buy a second property within a year of the firstLooking at houses in the $50K to $150K with $10-20K in repairs, the less the better for my first propertypro - start to build monthly cash flow which would result in buying the 2nd, 3rd, ... property quickercon  - slower equity build-up and would still be paying rent for my personal residenceI would love to know everyone's feedback and advice on which route would produce the best long term wealth. 

With $75K, you should be able to get 2 or 3 rental properties and capture $15K to $20K on each of them with straight up purchases. 

Last year my husband and I traveled for 8 months straight and stayed in tons of Airbnbs.