Keep it simple, search the 203k contractor database, you will/should find one in your area, call a few then pick best one.I know your investor wants his own contractor, but his contractor may be simply more expensive because he will have to consider carrying cost for project as the payments  and frequency of payments are regulated by lender.

Regarding your question about frequency of mailers, every 4 weeks works for most of our clients.

Just look at the forum homepage to see the frequency with which posts are replied to or posted and you'll see that there is no lack of action happening.I realize you're interested in the numbers -- with a Marketplace post, that data is available.

We have no plans right now to sell our AZ rentals, so we do set money aside for that stuff.I literally sat down one day and did what you did, just wrote down all the stuff we spend money on, estimated the cost, estimated the frequency, and then figured out how much to set aside each month. 

Indianapolis is a great marketIf you're single without anybody to answer to you might want to just rent out a property and then rent out rooms like a four bedroom two bath house, live rent freeGetting a real estate license might be a good idea so that you can get some respect in the marketplace because people respect people that a licensedIf you doing just wholesaling it might take you a long time to make money, but if you have say 500 a month for six months you may very well get some deals; @Dev Horn writes often about marketing from the wholesaling deals in "the rule of seven " and frequency of direct-mailI think the fastest start for new people is to go after "expired listings" and talk to homesellers that have little equity that are pretty with no work needed; your job is to help them sell on terms verses for cash on the lease to own; Then you find a buyer that "just missed financing" and wants to "rent to own"You generally make a 3% assignment fee usually in 45 days; that's much faster than wholesaling and you don't to deal with builders or Hard Money lenders,  just the buyer and sellerI train on lease option assignments so see the free training on My BP blog Reiskills Best of luck!

Given the region and frequency of hurricanes/flooding will I need some sort of history of how the property faired during bad weather or will they research that themselves?

What is the frequency you mail?

I have contacts with commercial brokers out of this particular state and I can tell the good from bad by the deals and frequency that they send me.

They have expired but as an estate from period to period they now are month to month under the same rent and frequency of payment until either landlord or tenant gives written termination notice.

I also review the frequency of repairs, as sometimes you will have one that has cost more over a shorter term.