I'm thinking now though that it may be more appropriate to attempt that a little further on down the road once my own personal risk tolerance could accept it.

I don't know if they still do it but if memory serves a few years ago TD Bank would do a HELOC on a rental in second position but only if it was titled in someone's personal name. 

The person worked for H&R Block, now works for TurboTax Live and is being honest about their skills: NOT QUALIFIED.

So why is the $2,500mnth person paying $250 and the other one paying $350 ??????

It was kind of a bad spot in my life at the time.

If you wanted to fund a portion of the down payment would you suggest a hard money lender, personal loan, etc.?

No reason to believe I won't receive $50 per month for the life of this fund. 

Matt that is the NMLS number for the company not for you personally  sounds like your a VA or something not a licensed lender..

Unfortunately, this problem waste a lot of my time that could be spent on other investments.I have used the same tax professional for many years and he is very educated, but also much older than me and it's hard for me to understand all the reasons he has expressed why is better to put the rental on my personal tax returns.

I also personally feel like I may take a step back from my main biz in about 15yrs..