Learn about real estate before making costly mistakes:1.

My main concern would be using HELOC on personal residence to make first real estate investment, not as concerned with the Roth/IRA but still don't want to make a big mistake on the first one. 

A simple mistake can cost you more money or time.Here's a pretty good guide: https://www.clarkcountyohio.gov/DocumentCenter/View/5210/CCO...

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.

@Jazzous Anderson try NARPM.comAlso, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.PM us if you’d like to discuss this logical approach in greater detail!

My worst appreciating property has appreciated ~$2700/month over its hold.  

I could probably get it for cheaper but just for now I want to see worst case scenario. 

However, it's important to remember this trend started in the not too distant past, and for a very long time before that the norm was separate rooms, so it's not surprising that there are actually considerable disadvantages of open floorplans and advantages of more traditional ones.Opening the kitchen to the rest of the house has to be one of the worst aspects of this trend.

Also do you have a private lender like family who can bail you out in worst scenario?