However if we were to wait and use 5K of cash flow instead to pay for something after 1 year of renting, would that decrease the "estimated repairs" number to $20K in that calculator or would it make no difference whether it's cash from the business or personal cash out of pocket as far as the cash on cash return calculation is concerned?

Coordinate with your PM to make sure you are both on the same page and wait to see what happens.

The cost for insurance could be a lot cheaper than running an LLC.Now if you have hundreds of thousands to millions in assets, it would be worthwhile to talk with an attorney.One last thing, if you have financing on said property, transferring it from your name into an LLC could trigger a due on sale clause, which means you would have to get new financing.

He wants us to wait even though he really is in the middle of the job right now.

I don't want to bribe her with thousands of bucks if I can help it. 

My question is would it be a bad move to purchase a home and rent it out while we wait for the neighborhood to improve?

Househack or wait until you have 20k.

I have been fortunate enough to be in this here real estate game for over 25 years as well as have some basic experience in BPO's (several thousand over the last several years).

I always wait to see them outside and go introduce myself to get the info on the other neighbors and see who is looking to sell.

If you wait until filing season to hire a CPA, it is too late to do effective tax planning or to develop an effective tax avoidance strategy.