It's up to you to decide if that extra effort is worthwhile.I believe the Airbnb vs Furnished Finder question really differs based on your market.

We told him we would give him an extra day but would be there on Wednesday to walk through, collect the keys, secure the house etc.

Only do this if you're prepared to fix whatever else the inspection uncovers, but inspectors are usually helpful and friendly when you ask for the inspection and not from a tenant complaint.

It is usually 88 degrees year around.

I'm considering getting out of the Mid-Term Rental Game.I purchased 30 apartments (two 10 units, a 6-unit, and a 4-unit) for the purpose of running them as Mid-Term rentals.Currently, half of them are being run as MTRs while the remaining are still LTRs.My MTRs average $1,600/month while the LTR rate $900/month.Now that I have some data, I wanted to compare apples to apples for MTR vs LTR revenue.After adjusting for the increase in Insurance, my VA for communicating managing, and supplies/increased repairs it's looking closer to $1,200 for MTR compared to LTRs $900.It's a lot of extra headaches for $300 more per month.I'm also having trouble refinancing these properties because banks hate seeing anything but LTR.

My initial thoughts are to spend money upgrading the kitchen and master bath; granite countertops, tile backsplash, maybe a pot filler over range, tile shower, extra windows?

We usually don't go with those institutions anyway...but your tenant may not know that.  

The extra financial commitment doesn’t worry me, its just the amount of debt that I will have that makes me nervous. 

The title company will either have an affliate they will send you to where your at in Chicago ( same underwriter usually) or hire a mobile notary service.. these are quite strange .

The self-filing mistakes don't usually appear until you get a letter from the IRS, sell the property and need to fix it, or talk to other real estate investors and then realize you are missing out on thousands of $ in tax savings to save a few hundred $ in filing fees ...