You'll certainly find more lenders wanting to lend in first position.Regardless, the new loan would need to be large enough to pay down the HELOC while also meeting the lender's guidelines for whatever lien position they were taking.I'm no lender...

The current tenant claims they were there when he moved in...... in going through my records, my move in agent and the tenants placing agent have no record of a move in condition sheet filled out by the tenant.Lease states that if the tenant does not submit one, the house is considered damage free.House bought in 5/2014..all new paint....one tenant previous for 12 months...this tenant for the remaining time until now.My agent did the walk through post last move out and did not note any issues where she felt I needed to repaint except one room, which I did.Since its so many walls in different rooms, the estimate is $1000 to repaint these areas.So the recent tenant is claiming they were there already and its normal wear and tear and is my responsibility to fix.My position is that there is no documentation of his claim and if he had just left them alone I could have fixed the issues way cheaper since it would have been done correctly from the start....it would have been way better to just leave a bunch of nail holes in the walls than have blotchy paint everywhereOpinions?

My current rental property has about 50000$ in equity but is not cash flow positive, doesn't cost anything but still no cash flow , another negative is that it is about 2000 miles away and makes it hard to deal with tenant issue, thankfully no major issues have come up YET.

There are so many people that just go online to register their pet, and there are many online websites that will provide a letter for this. 

Your county does not have a great website with all the online tools they should have, so you may need to do it OLD school and call them or go down there!

Are there things a newbie can do / provide that would be useful to those in a position to provide legitimate mentoring?

For the most case, for the stuff discussed on this website you don’t need a degree.

What would one recommend investing in a Major downtown, metropolitan area, like downtown LA or SD for generating positive cash flow?

if so, the focus on rent roll, your good credit, etc.According to what I saw on the VA website, you would be eligible for a VA loan for multifamily upto a fourplex if you lived in one of the units.Additionally, it is common for banks to consider the current rent rolls in the lending decision.

This will position yourself well so if the market does take a sharp decline you will be positioned to take advantage.