Reg D: When is it necessary for raising private debt?

[James Masotti]

Not sure if I should be posting this under the Private Lending forum or the legal forum, but figured this would be a start and we'll see what sort of answers it turns up.

I'm working on writing my investment proposal to take to some additional private money lenders. These are folks I have previous personal or professional relationships with and some of whom are accredited investors, but some are also not accredited. 

Curious to get the thoughts of others who have traveled down this path but what is that line where I need to be looking at a securities attorney and dealing with Reg D?

Also - What exactly is considered advertising and solicitation also? I'm guessing from the bit I've read so far that emailing and calling people I know about the opportunity to be a private lender is not a problem. However is putting a status up on LinkedIn or Facebook or BiggerPockets for that matter, explaining my business and then having a general statement like "Interested to find out how you can invest with me, contact me for more details" Is that considered advertising? These are status updates or posts or whatever you want to call it depending on the forum which are going to people that I have pre-existing connections with and doesn't in itself offer any sort of promises on return or anything.  I mean after all people are on BP pretty regularly asking for private funding and it doesn't seem like it's triggering Reg D for most of those people.

I know this is a lot and probably a dense topic, but appreciate the insights from anyone who is willing to share.