If he starts to make it a habit you tell him the next time you will just go ahead and evict.

Some don't have flood, loss of rental income etc...The tenants should have a renters policy to cover their own belongings, your policy does not cover their items.If you have loss of rental income, your policy will pay reimburse you the amount of rent you missed out on until the property is back in habitable condition.You will need to make a claim  on your own insurance first.

GCs are super busy here in the Bay Area, so that last bit might not be as vital in your area.

I agree with @Mike Dymski, savings and budget (especially for newer investors) is vital to an investor's growth.

You could joint venture with the owner and obtain an FHA 203k loan to make the improvements needed to make the house habitable.  

You will need to start from the forum and resource areas..then the podcasts..loads of loads of vital materials to digest!.. 

Not saying this is the case with you but I have had tenants who call for every little thing and after a while I disappear and only collect the rent or fix big issues affecting habitability or safety.

I have had partners in various business ventures and I really am a big believer in partnering I have a General contractor (unlicensed in my state ) but licensed in hawaii I have been working as his laborer on one of his projects in return he gives me a pretty good rate on my work and renovations I have four properties and he has dived into them and really been very valuablethere is a dark side to every story he has a bad habit of over promisinghe means well but he just cant get projects in on time even with me helping and I am there I can see how fast he moves and how hard he works and even with my help we are weeks behind.I dont get mad because I believe in the long run I will be able to estimate his estimate and figure out the actual completion timesanother dark side is that he knows a lot but he also has missed a few classes for example he installed my laminate flooring and he knows all about how to measure and accomodate walls that ride out and floor levelling but he is cutting around all the door jambs instead of cutting out underneath them.it looks like amateur hour.in the interest of time and money I am going to let this go this time in this apartment but the next apartment I will insist we use a saw and cut out underneath the jambswhat is my point in my rambling?

I agree with @Bob Ebaugh and @Tammy Vitale - $1k over asking is not that much, depending on how the property was priced.

I believe it has to be under 180 days, and although you can do several lease options in serial, my lawyer recommended against making that a habit or carrying it out too far.