I gave my contractor a deposit in December and final payment in January for a large structural repair job on a property that is partially personal (I live in one room) and partially business (my LLC) as a vacation rental.Now I need to send him a 1099 and send the IRS a 1096 (late on both of these, I recently found out), and figure out which tax year to apply the payments. 

Finally, I can buy a SFH all in closing/repairs for 13k.

Usually minor things aren't going to get you much but major repair items will, like the roof needs replaced or it has cracked rafters or floor joists. 

I usually travel to Austin and stay with family as well as spend a significant amount of time looking at and making repairs on my two properties.

This is a copy and paste from the lease I use: REPAIRS, PEST CONTROL AND DAMAGES.

The reason we didn't start with our property management company from the get go was that they were slow to respond to questions, and seemed like they would be a bit expensive on the repairs.

2) What methods do you use to determine a comfortable number pay the lessor per month while leaving enough  wiggle room to pay mortgage, cover for vacancies, repairs, taxes while having a good cash flow left over with the intent of saving this to use for the 20% down payment when the option is exercised.3) Would you pay for an inspection up front before the contract is signed, or wait until it's time to exercise the option?

Its listed as a SFH and is considered one by the county but has a 2 story duplex in the back that needs some extensive repairs from water damage but the actual house is in decent shape.

Most Property Management companies when there is a Repair & Maintenance issue, the either call someone to fix it and pass the bill onto you or they have a team of handymen/contractors that they will send to fix the issue and, depending on your agreement with them, bill you for it. 

Looking for a handyman that can do few repairs on a house we just purchased.