Following as we are looking at purchasing a resort cabin above Boise this summer/fall and worry about the seasonality of it all too.  

Simplified Scenario for example purposes:1) Sell for $700K with Mortgage of $300K2) Buy 1 property for $300K and $100K down3) Buy 2nd property for $300K and $100K down4) After fees it nets me $100K cash that I take outResult: I cover my minimum mortgage threshold by $100K but I fall $100K shy of Minimum Purchase Price AND I take out $100K in cash.

The guy you want to hire is too expensive for you to hire, and he doesn't really do what you want him to do (IE: Work with investors).You're falling into a common management fallacy... you think you can make someone into something he isn't by manipulating his income and the terms of engagement.

So if a home is $300,000 and has a sqft of 2900 to see if this qualifies is divide the list price of $330,000 / by the sqft of the home which in this ex is 2900 which is $113 per sqft ($330,000/2900sqft= $113.00 per sqft)  $113 falls between $77.00 and $143.00 doesn’t it?   

back deck is falling down, roof is leaking and needs to be redone, and all siding is dry rotted.  

I have had two transactions fall through in the last year because of buried oil tanks in the yards of properties.

To be honest, I have had inspections that were missing key things (like the inspector who was too robust/heavyset to go into the crawl space to discover that all the copper plumbing had been ripped out), others who found the obvious (the plumbing should be replaced...no duh) and others who were pretty useful (the chimney is falling over so it would be better to get the roofers to tear it out and cover which saved me a ton of money).

The example you gave and many things fall in a grey area.

Never ever heard of a company paying the lost rents as well like Tim said (unless you bought tenant skip insurance) but who knows lots of companies do lots of different things.I see lots of companies allowing the owner to make the final tenant selection like James mentioned and although it's crazy from a legal standpoint (opens the PM up to discrimination claims) they all do it so if anything goes wrong with the tenant they can fall back on the fact that the owner picked them (which is pretty smart).

Rami,Here is a link for you to learn a little regarding your dilemma: https://oncarrot.com/why-real-estate-deals-fall-through/?