I personally like to stay in mine for 3 days atleast while I setup to know my properties more intimately and to work out the bugs which would be problems for guests.

Sadly, it didn't work out, but there are some other products out there offering a similar idea.One of them is a relatively new product called Tellus (https://www.tellusapp.com/).

This is an expensive place and it's not drivable so everyone needs to arrange and pay for airfare.This is tough.When you did your research prior to purchasing, did you find other similar properties that were already successful or is this more of a hope everything will work out?

As far as what will work out is up to you. 

Sellers motivation shouldn't factor in what you can afford, thats a bonus if they will negotiate, but your numbers have to make sense to you and work out for multiple exit strategies (str, ltr, sell etc)Running the purchase numbers is pretty straightforward, use almost any online mortgage calculator, make sure you know taxes and insurance (taxes will go up a bit if it is currently owner occupied and you don't plan to live in it) Once you know your mortgage amount then start looking at other STR's in the same area and same size/amenities and see what they are getting per night and how many nights a month they are rented to calculate what you MAY be able to get.

Release guarantee if the tenant you place doesn't work out, let's say in the first 90 days and maybe 1/2 price for the first 180 days.

If you find a property and the numbers work out, then buy it. 

I suppose you could work out a plan with the tenants to do a more gradual increase of the rent rather than doing it all at once to be more income-friendly and to allow them to attempt to budget for the increase but you may also risk losing them anyway. 

It sounds like if you just structured it giving him commissions it would not really work out considering he clearly wants more involvement/skin in the game on the project.Maybe just split it LLC 50/50 and the commission savings is a preferred return over his split on the exit?

Ooh OohYou're making me nervous now hahaWe are looking forward to serving your vision Andrew.Thanks for being super prompt with our process and what is required to take the next step.Please keep in mind that Ohio Cashflow/our market and properties aren't for everyone so don't get disappointed if thing's don't work out and we mutually decide that taking the next step is not the right thing to do.To be honest, this tends to happen more often than the other way around but don't forget that even in those moments every decision is made with the investors best interests at heart.I'm super glad tho that you are considering Ohio Cashflow again after we initially connected almost 2 years.I've always said that "all good things take time" and what was once just a dream is now one of the most reputable and best branded turnkey companies in the country...