My friend and I are planning to buy an investment property (My second his first).

Quote from @Dmytro Shcherbitskyi: Hi everyone, I’m planning to syndicate my first real estate deal and would love some guidance. 

Speaking with a lender is a good plan, they can help you plan for the future.  

I’ve also thought of plans for a smaller scale venue too.

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.

Unless you negotiate a new contract or addendum with your PMC, they do NOT have to abide by any requests/demands you make that contradict what's written in the management contract.If they have in fact NOT followed the terms of their contract, then you'll want to send them something in writing pointing out the specific language in their contract that they violated and ask what they plan to do about it.If they fail to correct or address the issues, then you'll want to start looking for a new PMC.

We are looking into getting a fixer upper and plan to rent out our original residence ( Zillow says we can get $2700 median rent in our area ) while moving and fixing up the new house.

I would imagine most attorneys located around the MA, NH border area plan to make more than $200,000 per year.

Overall I think nationwide it’s getting very tough to get into the STR space and make money and the fact that a municipality can tank your business at any time calls for a strong back up plan from the start!

If you planned on moving out of a house and buy another property, as an example, you could pull a HELOC before you moved out and keep it as an emergency fund.