One is the $10,000 repair expenses.

Trying to save $$ so I can prepare emergency funds in case of any major repairs etc .

And 3 days a year I spend about 30 minutes pondering a repair, rent increase or turnover choice. 

If you can get all the bedbug containing furniture out of the place and it will sit for awhile (or let it sit while the other repairs are done) you may be able to avoid some cost, but if you want to get a paying tenant in sooner rather than later you will want to bite the bullet and get it well done.

This is because I'm concerned that even though the things in the house I can see look great things like the electrical, plumbing, or the foundation may need major repair if not immediately relatively soon. 

Tell him you'll give him a call :) This is one of the reasons why we tell tenants they need to vacate the property for any major repairs.  

During demo, if they open up a wall and find a leak that requires a change order. the change order should be specific to that repair and have a cost associated with it. 6.

Central A/C is damaged beyond repair and needed to be replaced, which can't be done economically or with coopperation of the HOA and other neiighboring owners.

Just be the absolute best host you can be for the first year -- communicate clearly and quickly, make sure cleaning is top-notch, make sure all amenities work (hot tub is hot, TV remotes have batteries, etc. etc.)

- What level of repairs are you willing to do?