Each deal comes with a different set of surprises even for the most experienced operators.Take your time and don't rush it. 

So, setting aside the cash flow he enjoyed for the last 40 years, he has a profit of $305,000.  

if anything then I would set a flat fee to pay them for their service and then if you do find a property that offers buyers agents money, in which almost all I have seen still do...then I would have the title company back out the amount you decided on and the agent gets the remainder of the amount of commission that's left over. 

I never liked Airbnb's or VRBO's pricing structure because it seemed more like they set a price that will get you booked so they can get paid, and not necessarily for the profitability of your listing.

It is not a set it and forget it thing though, you'll still need to be active and review monthly statements and manage things to make sure everything is running smoothly. 

I think if you set up your platform listings appropriately you will do well.You could also contact local wedding and event coordinators and make them aware of your listing.

It’s humbing and frustrating, but it also teaches you those guardrails you’ll want next time.. like thorough screening, a solid lease agreement that sets ground rules upfront, and maybe even setting aside a bit more cushion in reserves.Chicago’s got plenty of investor-friendly pockets.

Each county in the US has S8 rent limits per bedroom, set by HUD.

Quote from @Michael Poloncic: Three individuals signed a lease together, all friends, the lease is set up where each of them are expected to pay 1/3 of the rent.

Now, if you've already set up LLCs per property, then yes, have at least 1 checking account per LLC.For people who own their properties personally, keep personal accounts that are exclusive to RE activities so all of that activity stays separate from other personal transactions.