I hired a licensed contractor to assist me with a rehab. 

He created an event on BP — if you look under events, you should be able to see it and all the details.

They don't charge application fees or security deposits, don't do background checks - they take ANY S8 tenant no matter how bad they are:(You really want Class C and B-minus areas for solid S8 tenants.Let us know what else we can assist you with.

I'm interested in setting up either an S-CORP or LLC, but want to make sure i make the right choice so that I can secure the best tax benefits, while also setting myself up to get into the next investment. 

However, multifamily properties may offer more considerable long-term rewards if you're ready to take on the challenges of maintaining numerous units and are interested in gradually creating a larger revenue stream.The optimal decision ultimately comes down to your own investment objectives, risk tolerance, managerial skills, and the particular market dynamics of the regions you're thinking about.

Does creating an LLC for managing the first investment property will be favorable for me as far as getting approved by a lender for a comercial loan investment 5+ units?

You may see it on paper, but the reality is it's going vanish.If you're comfortable house hacking, probably a better choice.

If the person you are working with is "working under someone else" they may be a loan officer assistant or processor who are not required to have a NMLS number but that would mean they cannot discuss rates with you.

Create a compelling template, possibly offering them a discount if they sign by "X" date. 

I would imagine that if your friend created the listing, and then gave you permission, in writing outside of FF, to use it as her agent, you should be able to use their login to update the calendar, write up the description, etc.