Hey Laura,As far as benchmarks go, be sure not to limit yourself to what you see on AirDNA.

I discussed the idea of an LLC with a local banker and he indicated setting one up especially at this stage was something I could easily do so I submitted my application with the state already.

You need a set of specifications and a scope of work so that the work performed can be compared to the work required by your agreement.

If you find that you aren't up for active real estate investing there are passive options to invest by partnering with an active experienced investor, investing in a syndication as a limited partner, etc. 

. $2,500-$2,700 in rent but have a $1,900 mortgage (including current property taxes) plus $100 for insurance, plus a 10% chance of no one renting and another 10% set aside for repairs.After all that I'm in a range of breaking even or making $200 a month with this as a rental.

Unfortunately we did not set up the 1031 exchange prior to selling the house.

Whether it's an electrician, or yard person, title company, Property Manager, etc. usually getting a referral from another investor in that market helps limit our risk to "unknown" people. 

You must have a custodian for an IRA, and while you can self-direct it, you do have a middleman between you and your IRA. 401k does not require a custodian and can be set up as a trust with you being the trustee.

Either set aside funds, or try to screen tenants better - or both.

Your lender, perhaps with your help, should obtain a set of loan documents from a vetted source.