Quote from @Theodore Sutton: Check out the site meetup.com and also the events page on BP for meetings up in your area to meet people like this and build relationships.

My current situation is that I always flip with other people’s money.

I can see how an application fee per person can be a deterrent for applicants in my case whether for more upscale rentals people may see it as more normal.I am starting off as a non-refundable fee and measure the resistance, then adjust if needed.

Mentioning unique perks like 'Game Room,' 'Lake View,' or 'Pet-Friendly' can really draw people in.

I manage my own portfolio and have worked as a PM for a very successful individual but have never considered managing other peoples properties.

There's no step by step guide but there are key things : Learn: RE strategies, what interests you, what do people in your area need.Connect: find a mentor, accountability group and be around those doing what you want to do.Help: solve problems- do people need dealflow, property mgmt, construction expertise, etc. 

Last time I checked only people who have lost a home are those who do not pay.

Communication is easy people.

A4: If you pay as “friends and family” – then yes, need 1099s.Q5: I only need to send 1099s to people, not to LLCs, right?

Overall i am pretty sure that you and I are in agreement - people usually underestimate the expenses, so it is always good to err on the side of having more reserve.