But consulting with the town would be good to try to understand what they're permitting process is like.

I’m passionate about learning and improving my process to provide real value to investors, whether you’re focused on fix-and-flip, buy-and-hold, or any other strategy.Looking forward to your thoughts and insights!

Quote from @Nick Am: I own a rental property through a single member LLC (say LLC-A) and I am in process of purchasing another property under the same LLC-A.

But just hating on wholesaling in a wholesaling forum is so unbelievably pointless. its not dead per se  but it is starting to be regulated as it should.. oregon just passed their version. where to wholesale you now need a license and over site by the RE commission.. along with criminal back ground and a BOND.. and as we know not everyone can pass either of those with the bond being the tough one if you have bad credit your not getting a bond.

Whether you’re a mortgage broker, real estate broker, or running a private lending shop, what software and processes have been game-changers for you?

I think if you can nail that down you will be able to find a market easier.As a buy and hold investor some of the things that were important to me when deciding on a market were landlord tenant laws, price to rent ratio, housing demand, ability to build a team, large population 500K plus, multi-family availability and some other factors.take the process step by step and you will be fine. 

As others have stated, you are far better off working with an experienced Broker that can navigate for you during these tough times. 

Would it be possible to connect to discuss more about the process of purchasing property as a military investor? 

From what I have tried to read from a non partisan site (tough to find nowadays) I believe the issue has been insurance companies lost billions in the past five years and the past 5-10 years have had the most costly fires ever.

A combination of extremely tough long term tenant protections and the economics of short term renting being a lot more attractive.