because I'm thinking no one can really tell you when to sell your property, since it would be difficult to get a loan from a private/hard lender first off.

This would be better answered in a private setting with your tax professional to determine the best steps moving forward and structure.

My second question is for future private money lending.

Any advice for first time buyer on where to find private money and/or a good realtor/property managers in my area of purchase.  

Can we talk more in private message?

Be very clear with your lender rep about this point, and see what, if any options, are available with this outcome.If anyone would like a recommendation for a as-is based DSCR provider that I've had the most success with, please reach out privately.

I can get a conventional loan, however, I would prefer to use a hard money lender or private lender to fund my first deal.

Have you ever partnered with a private or hard money lender for a real estate deal?

My advice is don't take any national road tour class. 

The goal is to opt into as many broker sites/lists as possible, so they start sending you OMs, and you can start underwriting deals.Then, you can start scheduling tours on some of these deals.