(We live in an area that gets extremely hot in the summer and a working cooling system of some sort is a requirement on mortgages, but I've told him we don't have to buy one in our area.)

It is a popular vacation rental destination, you love it, you have successfully navigated the notoriously difficult Tahoe STR restrictions and you have all the systems in place.

Have redone the roof, siding, flooring, paint, added a fence, and upgraded the HVAC system.

Just having the support of your significant other is a gamechanger for you so look to avoid any un-necessary pressure to become business partners if they are not interested.For us, my wife’s strengths are developing and implementing process and systems.

I've had employees work for me remotely, hourly, so it wouldn't bother me - but there has to be a pretty decent framework in place or a good system of accountability for you to be sure you're getting what you're paying for.

There's an argument to be made for a sliding scale depending on the age of the home and the condition of the systems. 

did the seller have problems with the heating system (suggesting there may be water in the fuel which could suggest a leak). 

Just need to tune up the systems and she'll be ok.

In my market $5-6k should cover a roof and I can get a full HVAC system installed for just under $5k.

Im trying to find a good system and strategy to make some wins in this segment.